Chemical Industry and Engineering Progress ›› 2023, Vol. 42 ›› Issue (9): 4649-4666.DOI: 10.16085/j.issn.1000-6613.2022-1859
• Industrial catalysis • Previous Articles Next Articles
WANG Peng1(), SHI Huibing1, ZHAO Deming1, FENG Baolin1, CHEN Qian1, YANG Da2
Received:
2022-10-08
Revised:
2023-02-09
Online:
2023-09-28
Published:
2023-09-15
Contact:
WANG Peng
王鹏1(), 史会兵1, 赵德明1, 冯保林1, 陈倩1, 杨妲2
通讯作者:
王鹏
作者简介:
王鹏(1988—),男,博士,高级研发工程师,研究方向为羰基合成。E-mail:lzuwangpeng@163.com。
基金资助:
CLC Number:
WANG Peng, SHI Huibing, ZHAO Deming, FENG Baolin, CHEN Qian, YANG Da. Recent advances on transition metal catalyzed carbonylation of chlorinated compounds[J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4649-4666.
王鹏, 史会兵, 赵德明, 冯保林, 陈倩, 杨妲. 过渡金属催化氯代物的羰基化反应研究进展[J]. 化工进展, 2023, 42(9): 4649-4666.
Add to citation manager EndNote|Ris|BibTeX
URL: https://hgjz.cip.com.cn/EN/10.16085/j.issn.1000-6613.2022-1859
1 | ZHANG Shaoke, NEUMANN Helfried, BELLER Matthias. Synthesis of α,β-unsaturated carbonyl compounds by carbonylation reactions[J]. Chemical Society Reviews, 2020, 49(10): 3187-3210. |
2 | FRANKE Robert, SELENT Detlef, Armin BÖRNER. Applied hydroformylation[J]. Chemical Reviews, 2012, 112(11): 5675-5732. |
3 | MARINKOVIC Jakob Maximilian, RIISAGER Anders, FRANKE Robert, et al. Fifteen years of supported ionic liquid phase-catalyzed hydroformylation: Material and process developments[J]. Industrial & Engineering Chemistry Research, 2019, 58(7): 2409-2420. |
4 | PENG Jinbao, GENG Huiqing, WU Xiaofeng. The chemistry of CO: Carbonylation[J]. Chem, 2019, 5(3): 526-552. |
5 | PENG Jinbao, WU Fupeng, WU Xiaofeng. First-row transition-metal-catalyzed carbonylative transformations of carbon electrophiles[J]. Chemical Reviews, 2019, 119(4): 2090-2127. |
6 | LIU Dong, LIU Chao, LI Heng, et al. Direct functionalization of tetrahydrofuran and 1,4-dioxane: Nickel-catalyzed oxidative C(sp3)-H arylation[J]. Angewandte Chemie International Edition, 2013, 52(16): 4453-4456. |
7 | WANG Lecheng, CHEN Bo, WU Xiaofeng. Cobalt-catalyzed direct aminocarbonylation of ethers: Efficient access to α-amide substituted ether derivatives[J]. Angewandte Chemie International Edition, 2022, 61(23): e202203797. |
8 | WANG Peng, YANG Da, LIU Huan. Recent advances on carbonylation of 1,3-dienes[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3379. |
9 | WANG Pengzi, YANG Da, LIU Huanyu. Recent advances on the synthesis of β-lactams by involving carbon monoxide[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3448-3458. |
10 | BARNARD Christopher F J. Carbonylation of aryl halides: Extending the scope of the reaction[J]. Organic Process Research & Development, 2008, 12(4): 566-574. |
11 | LITTKE Adam F, FU Gregory C. Palladium-catalyzed coupling reactions of aryl chlorides[J]. Angewandte Chemie International Edition, 2002, 41(22): 4176-4211. |
12 | CAI Chaoxian, RIVERA Nelo R, BALSELLS Jaume, et al. An efficient catalyst for Pd-catalyzed carbonylation of aryl arenesulfonates[J]. Organic Letters, 2006, 8(22): 5161-5164. |
13 | WU Lipeng, FANG Xianjie, LIU Qiang, et al. Palladium-catalyzed carbonylative transformation of C(sp3)-X bonds[J]. ACS Catalysis, 2014, 4(9): 2977-2989. |
14 | WU Xiaofeng. Palladium-catalyzed carbonylative transformation of aryl chlorides and aryl tosylates[J]. RSC Advances, 2016, 6(87): 83831-83837. |
15 | WANG Justin, STROM Alexandra E, HARTWIG John F. Mechanistic studies of palladium-catalyzed aminocarbonylation of aryl chlorides with carbon monoxide and ammonia[J]. Journal of the American Chemical Society, 2018, 140(25): 7979-7993. |
16 | SERGEEV Alexey G, SPANNENBERG Anke, BELLER Matthias. Palladium-catalyzed formylation of aryl bromides: elucidation of the catalytic cycle of an industrially applied coupling reaction[J]. Journal of the American Chemical Society, 2008, 130(46): 15549-15563. |
17 | SCHOENBERG A, HECK R F. Palladium-catalyzed formylation of aryl, heterocyclic, and vinylic halides[J]. Journal of the American Chemical Society, 1974, 96(25): 7761-7764. |
18 | STROMNOVA Tat'yana A, MOISEEV Ilya I. Palladium carbonyl complexes[J]. Russian Chemical Reviews, 1998, 67(6): 485-514. |
19 | GARROU Philip E, HECK Richard F. The mechanism of carbonylation of halo(bis ligand)organoplatinum(Ⅱ), -palladium(Ⅱ), and -nickel(Ⅱ) complexes[J]. Journal of the American Chemical Society, 1976, 98(14): 4115-4127. |
20 | BRENNFUHRER Anne, NEUMANN Helfried, BELLER Matthias. Palladium-catalyzed carbonylation reactions of aryl halides and related compounds[J]. Angewandte Chemie International Edition, 2009, 48(23): 4114-4133. |
21 | GRUSHIN Vladimir V, ALPER Howard. Transformations of chloroarenes, catalyzed by transition-metal complexes[J]. Chemical Reviews, 1994, 94(4): 1047-1062. |
22 | ALONSO Francisco, BELETSKAYA Irina P, Miguel YUS. Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: A critical overview. Part 2: The Suzuki reaction[J]. Tetrahedron, 2008, 64(14): 3047-3101. |
23 | FABIOLA Barrios-Landeros, CARROW Brad P, HARTWIG John F. Effect of ligand steric properties and halide identity on the mechanism for oxidative addition of haloarenes to trialkylphosphine Pd(0) complexes[J]. Journal of the American Chemical Society, 2009, 131(23): 8141-8154. |
24 | CRISTINA Jimenez-Rodriguez, EASTHAM Graham R, COLE-HAMILTON David J. The methoxycarbonylation of aryl chlorides catalysed by palladium complexes of bis(di-tert-butylphosphinomethyl)benzene[J]. Dalton Transactions, 2005, 2005(10): 1826-1830. |
25 | MUNDAY Rachel H, MARTINELLI Joseph R, BUCHWALD Stephen L. Palladium-catalyzed carbonylation of aryl tosylates and mesylates[J]. Journal of the American Chemical Society, 2008, 130(9): 2754-2755. |
26 | SCHOENBERG A, HECK R F. Palladium-catalyzed amidation of aryl, heterocyclic, and vinylic halides[J]. The Journal of Organic Chemistry, 1974, 39(23): 3327-3331. |
27 | TONIOLO L, GRAZIANI M. Metals in organic syntheses. V. The gattermann-Koch synthesis of aromatic aldehydes promoted by CuCl(PPh3) n (n=0, 1 or 3). Is the cuprous complex necessary in the synthesis of tolualdehyde?[J]. Journal of Organometallic Chemistry, 1980, 194(2): 221-228. |
28 | BEDFORD Robin B, CAZIN Catherine S J, HOLDER Debbie. The development of palladium catalysts for C—C and C—heteroatom bond forming reactions of aryl chloride substrates[J]. Coordination Chemistry Reviews, 2004, 248(21/22/23/24): 2283-2321. |
29 | FU Leiqing, CAO Xiaoji, WAN Jieping, et al. Synthesis of enaminone-Pd(Ⅱ) complexes and their application in catalysing aqueous Suzuki-Miyaura cross coupling reaction[J]. Chinese Journal of Chemistry, 2020, 38(3): 254-258. |
30 | YAMADA Makito, SHIO Yasunori, AKIYAMA Toshiki, et al. Ligand-free Suzuki-Miyaura coupling reaction of an aryl chloride using a continuous irradiation type microwave and a palladium nanoparticle catalyst: Effect of a co-existing solid[J]. Green Chemistry, 2019, 21(16): 4541-4549. |
31 | WANG Tao, XU Kai, ZHANG Anan, et al. Buchwald-Hartwig amination of aryl chlorides catalyzed by trinuclear N-heterocyclic carbene-palladium (Ⅱ) complexes[J]. Chinese Journal of Organic Chemistry, 2018, 38(1): 259. |
32 | PUTHIARAJ Pillaiyar, Wha-Seung AHN. Ullmann coupling of aryl chlorides in water catalyzed by palladium nanoparticles supported on amine-grafted porous aromatic polymer[J]. Molecular Catalysis, 2017, 437: 73-79. |
33 | Christian PÉTRIER, GEMAL André L, LUCHE Jean-Louis. Ultrasounds in organic synthesi 31. A simple, high yield modification of the bouveault reaction[J]. Tetrahedron Letters, 1982, 23(33): 3361-3364. |
34 | XIAO Shuhuan, LIU Chen, SONG Bin, et al. Samarium-based Grignard-type addition of organohalides to carbonyl compounds under catalysis of CuI[J]. Chemical Communications, 2021, 57(50): 6169-6172. |
35 | IRANPOOR Nasser, FIROUZABADI Habib, Elham ETEMADI-DAVAN, et al. Palladium-catalysed reductive carbonylation of aryl halides with iron pentacarbonyl for synthesis of aromatic aldehydes and deuterated aldehydes[J]. Applied Organometallic Chemistry, 2015, 29(11): 719-724. |
36 | HUSER Marc, YOUINOU Marie-Thérès, OSBORN John A. Aktivierung der C—Cl-bindung: Katalytische carbonylierung von dichlormethan und chlorbenzol[J]. Angewandte Chemie, 1989, 101(10): 1427-1430. |
37 | Yehoshua BEN-DAVID, PORTNOY Moshe, MILSTEIN David. Formylation of aryl chlorides catalysed by a palladium complex[J]. Chemical Communications, 1989(23): 1816. |
38 | YAMAMOTO Takahiro, TOGO Hideo. One-pot preparation of aromatic amides, 4-arylthiazoles, and 4-arylimidazoles from arenes[J]. European Journal of Organic Chemistry, 2018, 2018(30): 4187-4196. |
39 | SATHE Pratima A, KARPE Aniket S, PARAB Aniket A, et al. Tandem synthesis of aromatic amides from styrenes in water[J]. Tetrahedron Letters, 2018, 59(29): 2820-2823. |
40 | SCHNYDER A, BELLER M, MEHLTRETTER G, et al. Synthesis of primary aromatic amides by aminocarbonylation of aryl halides using formamide as an ammonia synthon[J]. The Journal of Organic Chemistry, 2001, 66(12): 4311-4315. |
41 | KAWAMOTO Takuji, SATO Aoi, Ilhyong RYU. Photoinduced aminocarbonylation of aryl iodides[J]. Chemistry-A European Journal, 2015, 21(42): 14764-14767. |
42 | JU Jinhun, MISO Jeong, JEONGJU Moon, et al. Aminocarbonylation of aryl halides using a nickel phosphite catalytic system[J]. Organic Letters, 2007, 9(22): 4615-4618. |
43 | CHEUNG Chi Wai, LEENDERT PLOEGER Marten, HU Xile. Amide synthesis via nickel-catalysed reductive aminocarbonylation of aryl halides with nitroarenes[J]. Chemical Science, 2018, 9(3): 655-659. |
44 | WU Xiongyu, EKEGREN Jenny K, LARHED Mats. Microwave-promoted aminocarbonylation of aryl iodides, aryl bromides, and aryl chlorides in water[J]. Organometallics, 2006, 25(6): 1434-1439. |
45 | WANG Dongliang, GUO Wendi, ZHOU Qing, et al. Hydroaminocarbonylation of alkynes to produce primary α,β-unsaturated amides using NH4HCO3 dually as ammonia surrogate and Brønsted acid additive[J]. ChemCatChem, 2018, 10(19): 4264-4268. |
46 | BLANKSBY Stephen J, Barney ELLISON G. Bond dissociation energies of organic molecules[J]. Accounts of Chemical Research, 2003, 36(4): 255-263. |
47 | NASR ALLAH Tawfiq, PONSARD Louise, NICOLAS Emmanuel, et al. Catalytic challenges and strategies for the carbonylation of σ-bonds[J]. Green Chemistry, 2021, 23(2): 723-739. |
48 | YUAN Yang, WU Xiaofeng. Palladium-catalyzed carbonylative synthesis of N-heterocycles from 1-chloro-2-fluorobenzenes[J]. European Journal of Organic Chemistry, 2019, 2019(11): 2172-2175. |
49 | LAGERLUND Olof, LARHED Mats. Microwave-promoted aminocarbonylations of aryl chlorides using Mo(CO)6 as a solid carbon monoxide source[J]. Journal of Combinatorial Chemistry, 2006, 8(1): 4-6. |
50 | APPUKKUTTAN Prasad, AXELSSON Linda, VAN DER EYCKEN Erik, et al. Microwave-assisted, Mo(CO)6-mediated, palladium-catalyzed amino-carbonylation of aryl halides using allylamine: from exploration to scale-up[J]. Tetrahedron Letters, 2008, 49(39): 5625-5628. |
51 | TAKEUCHI Ryo, SUZUKI Katsunobu, SATO Nobuhiro. Palladium-catalyzed carbonylation of N-heteroaromatic chloride[J]. Journal of Molecular Catalysis, 1991, 66(3): 277-288. |
52 | Wolfgang MÁGERLEIN, INDOLESE Adriano F, BELLER Matthias. A more efficient catalyst for the carbonylation of chloroarenes[J]. Angewandte Chemie International Edition, 2001, 40(15): 2856-2859. |
53 | PERRY Robert J, WILSON B D. Palladium-catalyzed carbonylation and coupling reactions of aryl chlorides and amines[J]. The Journal of Organic Chemistry, 1996, 61(21): 7482-7485. |
54 | KIM Jang Sub, Ayusman SEN. Palladium(Ⅱ)-catalyzed synthesis of polyamides (aramids) from aromatic dichlorides, diamines, and carbon monoxide[J]. Journal of Molecular Catalysis A: Chemical, 1999, 143(1/2/3): 197-201. |
55 | WU Xiaofeng, NEUMANN Helfried, BELLER Matthias. Selective palladium-catalyzed aminocarbonylation of aryl halides with CO and ammonia[J]. Chemistry-A European Journal, 2010, 16(32): 9750-9753. |
56 | MARTINELLI Joseph R, CLARK Thomas P, WATSON Donald A, et al. Palladium-catalyzed aminocarbonylation of aryl chlorides at atmospheric pressure: The dual role of sodium phenoxide[J]. Angewandte Chemie International Edition, 2007, 46(44): 8460-8463. |
57 | Pierre-Louis LAGUEUX-TREMBLAY, FABRIKANT Alexander, ARNDTSEN Bruce A. Palladium-catalyzed carbonylation of aryl chlorides to electrophilic aroyl-DMAP salts[J]. ACS Catalysis, 2018, 8(6): 5350-5354. |
58 | Yehoshua BEN-DAVID, PORTNOY Moshe, MILSTEIN David. Chelate-assisted, palladium-catalyzed efficient carbonylation of aryl chlorides[J]. Journal of the American Chemical Society, 1989, 111(23): 8742-8744. |
59 | WANG Peng, YANG Ji, SUN Kangkang, et al. A general synthesis of aromatic amides via palladium-catalyzed direct aminocarbonylation of aryl chlorides[J]. Organic Chemistry Frontiers, 2022, 9(9): 2491-2497. |
60 | DUFAUD Varonique, Jean THIVOLLE-CAZAT, BASSET Jean-Marie. Palladium catalysed carbonylation of aryl chlorides to the corresponding methyl esters[J]. Chemical Communications, 1990(5): 426-427. |
61 | Wolfgang MÄGERLEIN, INDOLESE Adriano F, BELLER Matthias. Development of new palladium catalysts for the alkoxycarbonylation of aryl chlorides[J]. Journal of Organometallic Chemistry, 2002, 641(1/2): 30-40. |
62 | SCHAREINA Thomas, ZAPF Alexander, Alain COTTÉ, et al. An improved protocol for palladium-catalyzed alkoxycarbonylations of aryl chlorides with alkyl formates[J]. Advanced Synthesis & Catalysis, 2010, 352(7): 1205-1209. |
63 | SHIMOMAKI Katsuya, MURATA Kei, MARTIN Ruben, et al. Visible-light-driven carboxylation of aryl halides by the combined use of palladium and photoredox catalysts[J]. Journal of the American Chemical Society, 2017, 139(28): 9467-9470. |
64 | AI Hanjun, FRANKE Robert, WU Xiaofeng. Pd/C-catalyzed methoxycarbonylation of aryl chlorides[J]. Molecular Catalysis, 2020, 493: 111043. |
65 | VAN HAAREN Richard J, OEVERING Henk, KAMER Paul C J, et al. The mechanism for palladium catalyzed carbonylation of cinnamyl chloride[J]. Journal of Organometallic Chemistry, 2004, 689(23): 3800-3805. |
66 | TSUJI Jiro, KIJI Jitsuo, IMAMURA Shinzo, et al. Organic syntheses by means of noble metal compounds. VIII.1 catalytic carbonylation of allylic compounds with palladium chloride[J]. Journal of the American Chemical Society, 1964, 86(20): 4350-4353. |
67 | OKANO Tamon, OKABE Nobuyuki, KIJI Jitsuo. Palladium-catalyzed, atmospheric pressure carbonylation of allylic halides under the influence of sodium hydroxide or alkoxides. A facile synthesis of β,γ-unsaturated acids[J]. Bulletin of the Chemical Society of Japan, 1992, 65(10): 2589-2593. |
68 | PAUL Frederic, PATT Joe, HARTWIG John F. Palladium-catalyzed formation of carbon-nitrogen bonds. Reaction intermediates and catalyst improvements in the hetero cross-coupling of aryl halides and tin amides[J]. Journal of the American Chemical Society, 1994, 116(13): 5969-5970. |
69 | KIJI Jitsuo, OKANO Tamon, HIGASHIMAE Yukiko, et al. A convenient route to β,γ-unsaturated esters without formation of the α,β-isomers. palladium-catalyzed alkoxycarbonylation of allylic halides under alcohol-potassium carbonate tow-phase conditions[J]. Bulletin of the Chemical Society of Japan, 1996, 69(4): 1029-1031. |
70 | TROISI Luiginio, TOMMASI Sara, PERRONE Serena, et al. One-pot ester synthesis from allyl and benzyl halides and alcohols by palladium-catalyzed carbonylation[J]. Synthesis, 2012, 44(3): 423-430. |
71 | TSUJI Jiro, KIJI Jitsuo, MORIKAWA Masanobu. Organic syntheses by means of noble metal compounds III. Reaction of π-allylpalladium chloride complex with carbon monoxide[J]. Tetrahedron Letters, 1963, 4(26): 1811-1813. |
72 | ZAPF Alexander, BELLER Matthias. The development of efficient catalysts for palladium-catalyzed coupling reactions of aryl halides [J]. Chemical Communications. 2005(4): 431-440. |
73 | IMAMURA S, TSUJI J. Organic syntheses by means of noble metal compounds-XL: Palladium-catalysed carbonylation of allylic ethers[J]. Tetrahedron, 1969, 25(18): 4187-4195. |
74 | DENT W T, LONG R, WHITFIELD G H. 315. The carbonylation of allylic chlorides[J]. Journal of the Chemical Society, 1964, 0: 1588-1594. |
75 | MEDEMA D, VAN HELDEN R, KOHLL C F. Palladium-catalysed carbonylation of unsaturated compounds[J]. Inorganica Chimica Acta, 1969, 3: 255-265. |
76 | YAMAMOTO Akio. Palladium-catalyzed double and single carbonylation of aryl halides and allylic compounds[J]. Bulletin of the Chemical Society of Japan, 1995, 68(2): 433-446. |
77 | ZHANG Min, ZHAO Xiaoming, ZHENG Shengcai. Enantioselective domino reaction of CO2, amines and allyl chlorides under iridium catalysis: Formation of allyl carbamates[J]. Chemical Communications, 2014, 50(34): 4455-4458. |
78 | WU Fupeng, PENG Jinbao, FU Luyang, et al. Direct palladium-catalyzed carbonylative transformation of allylic alcohols and related derivatives[J]. Organic Letters, 2017, 19(19): 5474-5477. |
79 | WANG Peng, CAO Zhusong, WANG Yaxin, et al. Palladium-catalyzed carbonylation of allylic chlorides to β,γ-unsaturated esters/amides under mild conditions[J]. European Journal of Organic Chemistry, 2022, 2022(30): 204-208. |
80 | SCHOENBERG A, BARTOLETTI I, HECK R F. Palladium-catalyzed carboalkoxylation of aryl, benzyl, and vinylic halides[J]. Journal of Organic Chemistry, 1974, 39(23): 3318-3326. |
81 | HIDAI Masanobu, HIKITA Tomoji, WADA Yoshimasa, et al. Carboxymethylation of organic halides by palladium complexes under mild conditions[J]. Bulletin of the Chemical Society of Japan, 1975, 48(7): 2075-2077. |
82 | URATA Hisao, HU Nanxin, MAEKAWA Hisayuki, et al. Transition metal complex catalyzed carbonylation of organic halides in the presence of molecular sieves instead of base[J]. Tetrahedron Letters, 1991, 32(36): 4733-4736. |
83 | FOÀ M, FRANCALANCI F, GARDANO A, et al. Tetracarbonyl cobaltate ion supported on anion exchangers as a new heterogenized homogeneous catalyst: Synthesis of acids and esters from organic halides[J]. Journal of Organometallic Chemistry, 1983, 248(2): 225-230. |
84 | TUSTIN Gerald C, HEMBRE Robert T. Catalytic uses of iron pentacarbonyl: Formation of carboxylic acid derivatives[J]. Journal of Organic Chemistry, 1984, 49(10): 1761-1764. |
85 | ADAPA Srinivas R, PRASAD Chalasani S N. A mild and convenient preparation of t-butyl esters by carbonylation of arylhalogenomethyl derivatives[J]. Journal of the Chemical Society. Perkin Transactions 1, 1989(9): 1706-1707. |
86 | TRZECIAK Anna M, WOJTKOW Wojtków, CIUNIK Zbigniew, et al. Low-pressure carbonylation of benzyl bromide with palladium complexes modified with PNS (PNS=Ph2PCH2CH2C(O)NHC(CH3)2CH2SO3Li) or P(OPh)3. Structural identification of palladium-catalyst intermediate[J]. Catalysis Letters, 2001, 77(4): 245-249. |
87 | WU Xiaofeng, NEUMANN Helfried, BELLER Matthias. Palladium-catalyzed carbonylative coupling of benzyl chlorides with aryl boronic acids in aqueous media[J]. Tetrahedron Letters, 2010, 51(47): 6146-6149. |
88 | WU Xiaofeng, NEUMANN Helfried, BELLER Matthias. Palladium-catalyzed carbonylative suzuki coupling of benzyl halides with potassium aryltrifluoroborates in aqueous media[J]. Advanced Synthesis & Catalysis, 2011, 353(5): 788-792. |
89 | WU Xiaofeng, NEUMANN Helfried, BELLER Matthias. Palladium-catalyzed carbonylative coupling of benzyl chlorides with terminal alkynes to give 1,4-diaryl-3-butyn-2-ones and related furanones[J]. Organic & Biomolecular Chemistry, 2011, 9(23): 8003-8005. |
90 | TROISI Luigino, GRANITO Catia, ROSATO Francesca, et al. One-pot amide synthesis from allyl or benzyl halides and amines by Pd-catalysed carbonylation[J]. Tetrahedron Letters, 2010, 51(2): 371-373. |
91 | WU Xiaofeng, SCHRANCK Johannes, NEUMANN Helfried, et al. Palladium-catalyzed aminocarbonylation of benzyl chlorides using ammonia[J]. ChemCatChem, 2012, 4(1): 69-71. |
92 | RICHARDSON Jeffery, Eloise RILVIN-DERRICK, ORAM Niall. An efficient palladium-catalysed aminocarbonylation of benzyl chlorides[J]. Synlett, 2020, 31(4): 369-372. |
93 | TROISI Luigino, PINDINELLI Emanuela, STRUSI Valentina, et al. Synthesis and isomerization of N-α-aza-heteroaryl-β-lactams[J]. Tetrahedron, 2006, 62(51): 12064-12070. |
94 | TROISI Luigino, PINDINELLI Emanuela, STRUSI Valentina, et al. Stereoselective synthesis of 3,4-diaryl β-lactams[J]. Tetrahedron: Asymmetry, 2009, 20(3): 368-374. |
95 | WU Xiaofeng, WU Lipeng, JACKSTELL Ralf, et al. A general Palladium-catalyzed carbonylative synthesis of chromenones from salicylic aldehydes and benzyl chlorides[J]. Chemistry-A European Journal, 2013, 19(37): 12245-12248. |
96 | CASSAR L, FOÀ M, GARDANO A. The use of phase-transfer catalysis in palladium-catalyzed carbonylation of organic halides[J]. Journal of Organometallic Chemistry, 1976, 121(3): C55-C56. |
97 | OKANO T, UCHIDA I, NAKAGAKI T, et al. Carbonylation of benzyl chloride catalyzed by watersoluble palladium phosphine complex in a two-phase system[J]. Journal of Molecular Catalysis, 1989, 54(1): 65-71. |
98 | KOHLPAINTNER C W, BELLER M. Palladium-catalyzed carbonylation of benzyl chlorides to phenylacetic acids-a new two-phase process[J]. Journal of Molecular Catalysis A: Chemical, 1997, 116(1/2): 259-267. |
99 | PELLEGRINI S, CASTANET Y, MORTREUX A. Efficient methoxycarbonylation of benzyl chloride without external carbon monoxide: A further application of methyl formate in synthesis using PdCl2(PPh3)2 as catalyst[J]. Journal of Molecular Catalysis A: Chemical, 1999, 138(1): 103-106. |
100 | Ruben GAVIÑO, PELLEGRINI Sylvain, CASTANET Yves, et al. CO pressure as a key factor for the palladium-catalyzed methoxycarbonylation of benzyl chloride under mild conditions[J]. Applied Catalysis A: General, 2001, 217(1/2): 91-99. |
101 | PRYJOMSKA Iweta, BECHOWSKI Hubert Bartosz, CIUNIK Zbigniew, et al. Chemistry of palladium phosphinite (PPh2(OR)) and phosphonite (P(OPh)2(OH)) complexes: Catalytic activity in methoxycarbonylation and Heck coupling reactions[J]. Dalton Transactions (Cambridge, England: 2003), 2006(1): 213-220. |
102 | 陆军民. 苯乙酸生产方法综述[J]. 应用化工, 2001, 30(2): 10-12. |
LU Junmin. Summarization on the methods for production of phenylacetic acid[J]. Applied Chemical Industry, 2001, 30(2): 10-12. | |
103 | 陆军民. 我国苯乙酸的生产和市场分析[J]. 化工科技市场, 2004, 27(1): 8-12. |
LU Junming. The analysis of production and market on phenylacetic acid[J]. Chemical Technology Market, 2004, 27(1): 8-12. | |
104 | 梅付名, 李光兴, 蔡华强. 催化羰化合成苯乙酸的催化剂: CN1284406A[P]. 2001-02-21. |
MEI Fuming, LI Guangxing, CAI Huaqiang. Catalyst for catalytic carboxylation to synthesize phenylacetic acid: CN1284406A[P]. 2001-02-21. | |
105 | 傅宏祥, 李红兵, 周宏英, 等. 氯苄羰化制苯乙酸方法: CN1054584A[P]. 1995-11-01. |
FU Hongxiang, LI Hongbing, ZHOU Hongying, et al. Chlorobenzyl carbonylation making phenyl acetate method: CN1054584A[P]. 1995-11-01. | |
106 | 郭平, 宋传信, 贾宪洪, 等. 一种羰化合成苯乙酸反应釜: CN2434059Y[P]. 2001-06-13. |
GUO Ping, SONG Chuanxin, JIA Xianhong, et al. Carbonylation synthetized benzene acetic acid agitated reactor: CN2434059Y[P]. 2001-06-13. | |
107 | 郑晓来, 蒋景阳, 王兵, 等. 两相催化-均相催化多相化新进展[J]. 化学进展, 1997, 9(2): 111-122. |
ZHENG Xiaolai, JIANG Jingyang, WANG Bing, et al. Two-phase catalysis-recent advances in the heterogenization of homogeneous catalysis[J]. Progress in Chemistry, 1997, 9(2): 111-122. | |
108 | 金子林, 魏莉, 蒋景阳. 推进清洁生产技术的有效手段-均相催化多相化[J]. 石油化工, 2004, 33(5): 393-401. |
JIN Zilin, WEI Li, JIANG Jingyang. Multiphase catalysis-effective method for cleaner technology [J]. Petrochemical Technology, 2004, 33(5): 393-401. | |
109 | 陈金龙, 潘丙才, 张全兴, 等. 苯乙酸生产废水的治理与资源回收利用方法: CN1274684A[P]. 2000-11-29. |
CHEN Jinlong, PAN Bingcai, ZHANG Quanxing, et al. Method of treating waste water from production of phenylacetic acid and reusing resouce: CN1274684A[P]. 2000-11-29. | |
110 | STILLE John K, WONG Pui Kwan. Carboalkoxylation of aryl and benzyl halides catalyzed by dichlorobis(triphenylphosphine)palladium(Ⅱ)[J]. The Journal of Organic Chemistry, 1975, 40(4): 532-534. |
111 | LAPIDUS A L, ELISEEV O L, BONDARENKO T N, et al. Carbonylation of α-Haloketones[J]. Kinetics and Catalysis, 2004, 45(2): 234-238. |
112 | SURRY David S, BUCHWALD Stephen L. Dialkylbiaryl phosphines in Pd-catalyzed amination: A user’s guide[J]. Chemical Science, 2011, 2(1): 27-50. |
113 | CAVINATO G, PASQUALETTO M, RONCHIN L, et al. Palladium catalyzed hydrodechlorination of α-chloroacetophenones by hydrogen transfer from the H2O-CO system[J]. Journal of Molecular Catalysis A: Chemical, 1997, 125(1): 15-22. |
114 | CAVINATO G, TONIOLO L. PdCl2(PPh3)2]-PPh3 catalyzed regiospecific alkoxycarbonylation of α-chlorocyclohexylketone to β-ketoesters[J]. Journal of Molecular Catalysis A: Chemical, 1999, 143(1/2/3): 325-330. |
115 | LAPIDUS A L, ELISEEV O L, BONDARENKO T N, et al. Synthesis of β-keto esters by carbonylation of halomethylketones[J]. Synthesis, 2002, 2002(3): 317-319. |
116 | WAHL Benoit, BONIN Hélène, MORTREUX André, et al. A general and efficient method for the alkoxycarbonylation of α-chloro ketones[J]. Advanced Synthesis & Catalysis, 2012, 354(16): 3105-3114. |
117 | PERRONE Serena, SALOMONE Antonio, CAROLI Antonio, et al. Stereoselective synthesis of α-alkylidene β-oxo amides by palladium-catalyzed carbonylation[J]. European Journal of Organic Chemistry, 2014, 2014(27): 5932-5938. |
118 | TIETZE Lutz F. Domino reactions in organic synthesis[J]. Chemical Reviews, 1996, 96(1): 115-136. |
119 | WANG Shoucai, LI Xuan, ZANG Jiawang, et al. Palladium-catalyzed multistep tandem carbonylation/N-dealkylation/carbonylation reaction: Access to isatoic anhydrides[J]. The Journal of Organic Chemistry, 2019, 85(4): 2672-2679. |
120 | GAO Runduo, SHULER Scott A, WATSON Donald A. Tandem aza-Heck Suzuki and carbonylation reactions of O-phenyl hydroxamic ethers: Complex lactams via carboamination[J]. Chemical Science, 2021, 12(25): 8859-8864. |
121 | WAHL Benoit, GIBOULOT Steven, MORTREUX André, et al. Straightforward synthesis of allylated keto esters: The palladium-catalysed haloketone alkoxycarbonylation/allylation domino reaction[J]. Advanced Synthesis & Catalysis, 2012, 354(6): 1077-1083. |
122 | GIBOULOT Steven, LIRON Frédéric, PRESTAT Guillaume, et al. Pd-catalyzed domino carbonylative-decarboxylative allylation: An easy and selective monoallylation of ketones[J]. Chemical Communications, 2012, 48(47): 5889-5891. |
123 | WAHL Benoit, PHILIPSON Yann, BONIN Hélène, et al. Synthesis of α-alkylated β-ketoesters by alkoxycarbonylation/Michael addition domino reaction[J]. The Journal of Organic Chemistry, 2013, 78(4): 1547-1552. |
124 | MIURA Masahiro, OKURO Kazumi, HATTORI Ayako, et al. Carbonylation of vinyl halides with carbonylcobalt[J]. Journal of the Chemical Society, Perkin Transactions 1, 1989(1): 73-76. |
125 | RICHARD David J, SCHIAVI Bruno, JOULLIE Madeleine M. Synthetic studies of roquefortine C: Synthesis of isoroquefortine C and a heterocycle[J]. Proceedings of the National Academy of Sciences of the United States of America, 2004, 101(33): 11971-11976. |
126 | LASRI Jamal, MUKHOPADHYAY Suman, M Adflia Januário CHARMIER, et al. Efficient regioselective synthesis of 4- and 5-substituted isoxazoles under thermal and microwave conditions[J]. Journal of Heterocyclic Chemistry, 2008, 45(5): 1385-1389. |
127 | OWEN L N, H M Babatunde SOMADE. 191. Olefinic acids. Part II. The reactivity of α-bromoacrylic acid and some related compounds[J]. Journal of the Chemical Society (Resumed), 1947, 0: 1030-1034. |
128 | SUN Peipei, CHANG Mengyang, CHIANG Michael Y, et al. A facile route to polysubstituted N-benzyl pyroglutamates[J]. Organic Letters, 2003, 5(10): 1761-1763. |
129 | UTAKA Masanori, KONISHI Satoshi, MIZUOKA Ami, et al. Asymmetric reduction of the prochiral carbon-carbon double bond of methyl 2-chloro-2-alkenoates by use of fermenting bakers' yeast[J]. The Journal of Organic Chemistry, 1989, 54(21): 4989-4992. |
130 | CHANG Mengyang, SUN Peipei, CHEN Shui-Tein, et al. A facile synthesis of 3-aryl pyroglutamic acid. Facile synthesis of baclofen and chlorpheg[J]. Tetrahedron Letters, 2003, 44(28): 5271-5273. |
131 | MCNULTY James, MAO Justin. On the direct 2,3-hydroxyl-group differentiation of tartaric acid esters[J]. Tetrahedron Letters, 2002, 43(21): 3857-3861. |
132 | DOLLT Heribert, ZABEL Volker. Optically pure aminopolyols and polyoxamic acid derivatives from aziridine-2-carboxylates[J]. Australian Journal of Chemistry, 1999, 52(4): 259-270. |
133 | MIRONIUK-PUCHALSKA E, KOLACZKOWSKA E, SAS W. Synthesis of (±)-branched-chain azaisonucleosides via Michael addition of 5-nitro-2,2-pentamethylene-1,3-dioxane to methyl 2-bromoacrylate[J]. Tetrahedron Letters, 2002, 43(46): 8351-8354. |
134 | SPEZIALE A J, RATTS K W. Reaction of phosphorus compounds. V. Resonance-stabilized α-halomethylenephosphoranes[J]. The Journal of Organic Chemistry, 1963, 28(2): 465-469. |
135 | WADSWORTH William S, EMMONS William D. The utility of phosphonate carbanions in olefin synthesis[J]. Journal of the American Chemical Society, 1961, 83(7): 1733-1738. |
136 | GRISON Claude, Stéphane GENÈVE, COUTROT Philippe. Enantioselective synthesis of α,β-unsaturated γ- and δ-lactams[J]. Tetrahedron Letters, 2001, 42(23): 3831-3834. |
137 | MICHIDA Makoto, TORIUMI Takako, MUKAIYAMA Teruaki. A convenient method for the synthesis of (Z)-α-haloacrylates: Lewis base-catalyzed carbonyl olefination using α-halo-C,O-bis(trimethylsilyl)ketene acetals[J]. Tetrahedron Letters, 2009, 50(26): 3261-3262. |
138 | ARTHUIS Martin, LECUP Anne, ROULLAND Emmanuel. Pd0-Catalyzed carbonylation of 1,1-dichloro-1-alkenes, a new selective access to Z-α-chloroacrylates[J]. Chemical Communications, 2010, 46(41): 7810-7812. |
139 | SUMINO Shuhei, FUSANO Akira, FUKUYAMA Takahide, et al. Carbonylation reactions of alkyl iodides through the interplay of carbon radicals and Pd catalysts[J]. Accounts of Chemical Research, 2014, 47(5): 1563-1574. |
140 | HUSER Marc, YOUINOU Marie T, OSBORN John A. Chlorocarbon activation: Catalytic carbonylation of dichloromethane and chlorobenzene[J]. Angewandte Chemie International Edition, 1989, 28(10): 1386-1388. |
141 | TAKEUCHI R, TSUJI Y, WATANABE Y. Platinum complex-catalysed carbonylations of organic iodides having β-hydrogens attached to sp3-carbons[J]. Journal of the Chemical Society, Chemical Communications, 1986, 4: 351-352. |
142 | Ilhyong RYU, KUSANO Kazuya, OGAWA Akiya, et al. Free radical carbonylation. Efficient trapping of carbon monoxide by carbon radicals[J]. Journal of the American Chemical Society, 1990, 112(3): 1295-1297. |
143 | JIA Yingping, CUI Yingna, YIN Jingmei, et al. Cobalt-catalyzed photopromoted carbonylation of chloroalkanes in the presence of KI[J]. Chinese Chemical Letters, 2010, 21(9): 1033-1036. |
144 | WANG Hongwei, JIA Yingping, GAO Dabin, et al. Photo-promoted carbonylation of chloroalkanes with carbon monoxide by non-precious metal catalysts[J]. Chinese Chemical Letters, 2007, 18(7): 795-798. |
145 | WANG Peng, WANG Yaxin, NEUMANN Helfried, et al. Rh-catalyzed alkoxycarbonylation of unactivated alkyl chlorides[J]. Chemical Science, 2022, 13(45): 13459-13465. |
[1] | ZHANG Mingyan, LIU Yan, ZHANG Xueting, LIU Yake, LI Congju, ZHANG Xiuling. Research progress of non-noble metal bifunctional catalysts in zinc-air batteries [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 276-286. |
[2] | SHI Yongxing, LIN Gang, SUN Xiaohang, JIANG Weigeng, QIAO Dawei, YAN Binhang. Research progress on active sites in Cu-based catalysts for CO2 hydrogenation to methanol [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 287-298. |
[3] | XIE Luyao, CHEN Songzhe, WANG Laijun, ZHANG Ping. Platinum-based catalysts for SO2 depolarized electrolysis [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 299-309. |
[4] | YANG Xiazhen, PENG Yifan, LIU Huazhang, HUO Chao. Regulation of active phase of fused iron catalyst and its catalytic performance of Fischer-Tropsch synthesis [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 310-318. |
[5] | WANG Lele, YANG Wanrong, YAO Yan, LIU Tao, HE Chuan, LIU Xiao, SU Sheng, KONG Fanhai, ZHU Canghai, XIANG Jun. Influence of spent SCR catalyst blending on the characteristics and deNO x performance for new SCR catalyst [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 489-497. |
[6] | DENG Liping, SHI Haoyu, LIU Xiaolong, CHEN Yaoji, YAN Jingying. Non-noble metal modified vanadium titanium-based catalyst for NH3-SCR denitrification simultaneous control VOCs [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 542-548. |
[7] | ZHANG Tingting, ZUO Xuqian, TIAN Lingdi, WANG Shimeng. Construction method of volatile organic compounds emission inventory and factor database in chemical industry park [J]. Chemical Industry and Engineering Progress, 2023, 42(S1): 549-557. |
[8] | CHENG Tao, CUI Ruili, SONG Junnan, ZHANG Tianqi, ZHANG Yunhe, LIANG Shijie, PU Shi. Analysis of impurity deposition and pressure drop increase mechanisms in residue hydrotreating unit [J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4616-4627. |
[9] | ZHANG Qi, ZHAO Hong, RONG Junfeng. Research progress of anti-toxicity electrocatalysts for oxygen reduction reaction in PEMFC [J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4677-4691. |
[10] | GE Quanqian, XU Mai, LIANG Xian, WANG Fengwu. Research progress on the application of MOFs in photoelectrocatalysis [J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4692-4705. |
[11] | WANG Weitao, BAO Tingyu, JIANG Xulu, HE Zhenhong, WANG Kuan, YANG Yang, LIU Zhaotie. Oxidation of benzene to phenol over aldehyde-ketone resin based metal-free catalyst [J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4706-4715. |
[12] | GE Yafen, SUN Yu, XIAO Peng, LIU Qi, LIU Bo, SUN Chengying, GONG Yanjun. Research progress of zeolite for VOCs removal [J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4716-4730. |
[13] | LI Dongze, ZHANG Xiang, TIAN Jian, HU Pan, YAO Jie, ZHU Lin, BU Changsheng, WANG Xinye. Research progress of NO x reduction by carbonaceous substances for denitration in cement kiln [J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4882-4893. |
[14] | XIANG Yang, HUANG Xun, WEI Zidong. Recent progresses in the activity and selectivity improvement of electrocatalytic organic synthesis [J]. Chemical Industry and Engineering Progress, 2023, 42(8): 4005-4014. |
[15] | WANG Yaogang, HAN Zishan, GAO Jiachen, WANG Xinyu, LI Siqi, YANG Quanhong, WENG Zhe. Strategies for regulating product selectivity of copper-based catalysts in electrochemical CO2 reduction [J]. Chemical Industry and Engineering Progress, 2023, 42(8): 4043-4057. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||
京ICP备12046843号-2;京公网安备 11010102001994号 Copyright © Chemical Industry and Engineering Progress, All Rights Reserved. E-mail: hgjz@cip.com.cn Powered by Beijing Magtech Co. Ltd |