Chemical Industry and Engineering Progress ›› 2018, Vol. 37 ›› Issue (10): 3832-3842.DOI: 10.16085/j.issn.1000-6613.2017-2302
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YU Qinwei1,2, HUI Feng1,2, ZHANG Qian1,2, YUAN Jun1,2, WANG Weiqiang1,2, ZHAO Fengwei1,2, YANG Jianming1,2, LÜ Jian1,2
Received:2017-11-07
Revised:2018-02-22
Online:2018-10-05
Published:2018-10-05
余秦伟1,2, 惠丰1,2, 张前1,2, 袁俊1,2, 王为强1,2, 赵锋伟1,2, 杨建明1,2, 吕剑1,2
通讯作者:
吕剑,研究员,博士生导师,主要从事有机化工研究;杨建明,博士,研究员,硕士生导师,主要从事催化合成研究。
作者简介:余秦伟(1985-),男,博士研究生,副研究员,主要从事应用催化研究。E-mail:qinweiyu204@163.com。
基金资助:CLC Number:
YU Qinwei, HUI Feng, ZHANG Qian, YUAN Jun, WANG Weiqiang, ZHAO Fengwei, YANG Jianming, LÜ Jian. Progress in the catalyst for reductive amination of alcohol[J]. Chemical Industry and Engineering Progress, 2018, 37(10): 3832-3842.
余秦伟, 惠丰, 张前, 袁俊, 王为强, 赵锋伟, 杨建明, 吕剑. 醇还原胺化反应催化剂研究进展[J]. 化工进展, 2018, 37(10): 3832-3842.
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URL: https://hgjz.cip.com.cn/EN/10.16085/j.issn.1000-6613.2017-2302
| [1] LAWRENCE S A. Amines:synthesis, properties and applications[M]. London:Cambridge University Press, 2004:450. [2] YANG L C, WANG Y N, ZHANG Y, et al. Acid-assisted Ru-catalyzed enantioselective amination of 1,2-diols through borrowing hydrogen[J]. ACS Catalysis, 2017, 7(1):93-97. [3] IMM S, BAEHN S, NEUBERT L, et al. An efficient and general synthesis of primary amines by ruthenium-catalyzed amination of secondary alcohols with ammonia[J]. Angewandte Chemie International Edition, 2010, 49(44):8126-8129. [4] GUNANATHAN C, MILSTEIN D. Selective synthesis of primary amines directly from alcohols and ammonia[J]. Angewandte Chemie International Edition, 2008, 47(45):8661-8664. [5] PINGEN D, MUELLER C, VOGT D. Direct amination of secondary alcohols using ammonia[J]. Angewandte Chemie International Edition, 2010, 49(44):8130-8133. [6] NAKAGAWA N, DERRAH E J, SCHELWIES M, et al. Triphos derivatives and diphosphines as ligands in the ruthenium-catalyzed alcohol amination with NH3[J]. Dalton Transactions, 2016, 45(16):6856-6865. [7] HAMID M H S A, ALLEN C L, LAMB G W, et al. Ruthenium-catalyzed N-alkylation of amines and sulfonamides using borrowing hydrogen methodology[J]. Journal of the American Chemical Society, 2009, 131(5):1766-1774. [8] LAMB G W, WATSON A J A, JOLLEY K E, et al. Borrowing hydrogen methodology for the conversion of alcohols into N-protected primary amines and in situ deprotection[J]. Tetrahedron Letter, 2009, 50(26):3374-3377. [9] LEE C C, CHU W Y, LIU Y H, et al. Coordination and catalytic activity of ruthenium complexes containing tridentate P, N, O ligands[J]. European Journal of Inorganic Chemistry, 2011, 31:4801-4806. [10] SAHLI Z, SUNDARARAJU B, ACHARD M, et al. Rutheniumcatalyzed reductive amination of allylic alcohols[J]. Organic Letter, 2011, 13(15):3964-3967. [11] LUO J Y, WU M Y, XIAO F H, et al. Ruthenium-catalyzed direct amination of alcohols with tertiary amines[J]. Tetrahedron Letter, 2011, 52(21):2706-2709. [12] LEE C C, LIU S T. Preparation of secondary and tertiary amines from nitroarenes and alcohols[J]. Chemical Communications, 2011, 47(24):6981-6983. [13] BITSI G, SCHLEIFFER E, ANTONI F, et al. N-alkylation d'amines en catalyse homogène. Synthèse de mono-et de diamines cycliques[J]. Journal of Organometallic Chemistry, 1989, 373(3):343-352. [14] IMM S, BAEHN S, ZHANG M, et al. Improved ruthenium-catalyzed amination of alcohols with ammonia:Synthesis of diamines and amino esters[J]. Angewandte Chemie International Edition, 2011, 50(33):7599-7603. [15] MARICHEV K O, TAKACS J M. Ruthenium-catalyzed amination of secondary alcohols using borrowing hydrogen methodology[J]. ACS Catalysis, 2016, 6(4):2205-2210. [16] STÅLSMEDEN A S, VÁZQUEZ J L B, VAN WEERDENBURG K, et al. Glycerol upgrading via hydrogen borrowing:Direct ruthenium-catalyzed amination of the glycerol derivative solketal[J]. ACS Sustainable Chemistry & Engineering, 2016, 4(10):5730-5736. [17] DEFIEBER C, ARIGER M A, MORIEL P, et al. Iridium-catalyzed synthesis of primary allylic amines from allylic alcohols:sulfamic acid as ammonia equivalent[J]. Angewandte Chemie International Edition, 2007, 46(17):3139-3143. [18] LAFRANCE M, ROGGEN M, CARREIRA E M. Direct, enantioselective iridium-catalyzed allylic amination of racemic allylic alcohols[J]. Angewandte Chemie International Edition, 2012, 51(14):3470-3473. [19] ROGGEN M, CARREIRA E M. Stereospecific substitution of allylic alcohols to give optically active primary allylic amines:unique reactivity of a (P,alkene)Ir complex modulated by iodide[J]. Journal of the American Chemical Society, 2010, 132(34):11917-11919. [20] FUJITA K, LI Z Z, OZEKI N, et al. N-alkylation of amines with alcohols catalyzed by a Cp*Ir complex[J]. Tetrahedron Letters, 2003, 44(13):2687-2690. [21] BERLINER M A, DUBANT S P A, MAKOWSKI T, et al. Use of an iridium-catalyzed redox-neutral alcohol-amine coupling on kilogram scale for the synthesis of a GlyT1 inhibitor[J]. Organic Process Research & Development, 2011, 15(5):1052-1062. [22] FUJITA K I, ENOKI Y, YAMAGUCHI R. Cp*Ir-catalyzed N-alkylation of amines with alcohols. A versatile and atom economical method for the synthesis of amines[J]. Tetrahedron, 2008, 64(8):1943-1954. [23] FUJITA K I, YAMAMOTO K, YAMAGUCHI R. Oxidative cyclization of amino alcohols catalyzed by a Cp*Ir complex. Synthesis of indoles, 1,2,3,4-tetrahydroquinolines, and 2,3,4,5-tetrahydro-1-benzazepine[J]. Organic Letter, 2002, 4(16):2691-2694. [24] CHANG Y H, FU C F, LIU Y H, et al. Synthesis, characterization and catalytic activity of saturated and unsaturated N-heterocyclic carbene iridium(Ⅰ) complexes[J]. Dalton Transactions, 2009(5):861-867. [25] DU Z, YAN Y, FU Y, et al. Palladium-catalyzed direct amination of allylic alcohols in aqueous media[J]. Asian Journal of Organic Chemistry, 2016, 5(6):812-818. [26] JING J, HUO X, SHEN J, et al. Direct use of allylic alcohols and allylic amines in palladium-catalyzed allylic amination[J]. Chemical Communications, 2017, 53(37):5151-5154. [27] LEE E E, BATEY R A. Palladium-catalyzed[3,3] sigmatropic rearrangement of(allyloxy)iminodiazaphospholidines:allylic transposition of C-O and C-N functionality[J]. Angewandte Chemie International Edition, 2004, 43(14):1865-18687. [28] KRESSIERER C J, MULLER T J J. The first one-pot Alder-ene-reductive amination sequence[J]. Tetrahedron Letter, 2004, 45(10):2155-2158. [29] YU X C, JIANG L, LI Q, et al. Palladium-catalyzed N-alkylation of amides and amines with alcohols employing the aerobic relay race methodology[J]. Chinese Journal of Chemistry, 2012, 30(10):2322-2332. [30] MARTINEZ-ASENCIO A, RAMON D J, YUS M. N-alkylation of poor nucleophilic amines and derivatives with alcohols by a hydrogen autotransfer process catalyzed by copper(Ⅱ) acetate:scope and mechanistic considerations[J]. Tetrahedron, 2011, 67(17):3140-3149. [31] REDDY C R, MADHAVI P P, REDDY A S. Molybdenum(Ⅴ) chloride-catalyzed amidation of secondary benzyl alcohols with sulfonamides and carbamates[J]. Tetrahedron Letter, 2007, 48(40):7169-7172. [32] EMAYAVARAMBAN B, ROY M, SUNDARARAJU B. Iron-catalyzed allylic amination directly from allylic alcohols[J]. Chemistry-A European Journal, 2016, 22(12):3952-3955. [33] HIKAWA H, IJICHI Y, KIKKAWA S, et al. Cobalt(Ⅱ)/TPPMScatalyzed dehydrative nucleophilic substitution of alcohols in water[J]. European Journal of Organic Chemistry, 2017(3):465-468. [34] NOWROUZI N, JONAGHANI M Z. Highly selective monoN-benzylation and amidation of amines with alcohols or carboxylic acids using the Ph2PCl/I2/imidazole reagent system[J]. Canadian Journal of Chemistry, 2012, 90(6):498-509. [35] XU Q, LI Q, ZHU X G, et al. Green and scalable aldehyde-catalyzed transition metal-free dehydrative N-alkylation of amides and amines with alcohols[J]. Advanced Synthesis & Catalysis, 2013, 355(1):73-80. [36] MONTGOMERY S L, MANGAS-SANCHEZ J, THOMPSON M P, et al. Direct alkylation of amines with primary and secondary alcohols through biocatalytic hydrogen borrowing[J]. Angewandte Chemie International Edition, 2017, 56(35):10491-10494. [37] FISCHER A, MALLAT T, BAIKER A. Amination of diols and polyols to acyclic amines[J]. Catalysis Today, 1997, 37(2):167-189. [38] CHO J H, PARK J H, CHANG T S, et al. Reductive amination of 2-propanol to monoisopropylamine over Co/γ-Al2O3 catalysts[J]. Applied Catalysis A:General, 2012, 417-418:313-319. [39] SEWELL G, O'CONNOR C, STEEN E V. Reductive amination of ethanol with silica-supported cobalt and nickel catalysts[J]. Applied Catalysis A:General, 1995, 125(1):99-112. [40] ZHANG Y, BAI G, YAN X, et al. Amination of ethanolamine over cobalt modified H-ZSM-5 catalysts[J]. Catalysis Communication, 2007, 8(7):1102-1106. [41] FISCHER A, MACIEJEWSKI M, BGI T, et al. Cobalt-catalyzed amination of 1,3-propanediol:effects of catalyst promotion and use of supercritical ammonia as solvent and reactant[J]. Journal of Catalysis, 1999, 183(2):373-383. [42] JENZER G, MALLAT T, BAIKER A. Cobalt-catalyzed amination of 1,3-cyclohexanediol and 2,4-pentanediol in supercritical ammonia[J]. Catalysis Letters, 1999, 61(3):111-114. [43] FISCHER A, MALLAT T, BAIKER A. Synthesis of 1,4-diaminocyclohexane in supercritical ammonia[J]. Journal of Catalysis, 1999, 182(2):289-291. [44] LIU Y, ZHOU K, SHU H, et al. Switchable synthesis of furfurylamine and tetrahydrofurfurylamine from furfuryl alcohol over Raney nickel[J]. Catalysis Science & Technology, 2017, 7(18):4129-4135. [45] WANG W Q, YU Q W, ZHANG Q, et al. Reductive amination of 2-amino-2-methyl-1-propanol and ammonia to produce 2-methyl-1,2-propanediamine over Raney nickel catalyst[J]. Chemistry Select, 2017, 2(28):8818-8823. [46] KING S W. Reductive amination catalysts:US5750790[P]. 1998-03-12. [47] ALONSO F, RIENTE P, YUS M. Nickel nanoparticles in hydrogen transfer reactions[J]. Accounts of Chemical Research, 2011,44(5):379-391. [48] FISCHER A, MALLAT T, BAIKER A. Nickel-catalyzed amination of 1,3-propanediols differently substituted at C2-position:influence of reactant structure on diamine production[J]. Journal of Molecular Catalysis A:Chemical, 1999,149(1/2):197-204. [49] CANO R, RAMON D J, YUS M. Impregnated ruthenium on magnetite as a recyclable catalyst for the N-alkylation of amines, sulfonamides, sulfinamides, and nitroarenes using alcohols as electrophiles by a hydrogen autotransfer process[J]. The Journal of Organic Chemistry, 2011, 76(14):5547-5557. [50] NIEMEIER J, ENGEL R V, ROSE M. Is water a suitable solvent for the catalytic amination of alcohols?[J]. Green Chemistry, 2017, 19(12):2839-2845. [51] STIBAL D, SA J, VAN B J A. One-pot photo-reductive N-alkylation of aniline and nitroarene derivatives with primary alcohols over Au-TiO2[J]. Catalysis Science & Technology, 2013, 3(1):94-98. [52] DEMIDOVA Y S, SUSLOV E V, SIMAKOVA I L, et al. Selectivity control in one-pot myrtenol amination over Au/ZrO2 by molecular hydrogen addition[J]. Journal of Molecular Catalysis A:Chemical, 2017, 426(Part A):60-67. [53] DEMIDOVA Y S, SUSLOV E V, SIMAKOVA I L, et al. Promoting effect of alcohols and formic acid on Au-catalyzed one-pot myrtenol amination[J]. Journal of Molecular Catalysis, 2017, 433:414-419. [54] PERA-TITUS M, YAN Z, TOMER A, et al. A Pd/CeO2 "H2 pump" for the direct amination of alcohols[J]. ChemCatChem, 2016,8(21):3347-3352. [55] KAMMELAR R W F, TIMMERMANS H J A R, FRIKKEE-DEKKER P J, et al. Preparation of lactose-containing oligosaccharides as surfactants, emulsifiers, and dispersants:WO9730063A2[P]. 1997-08-21. [56] KNOEFEL N D, ROTHFUSS H, WILLENBACHER J, et al. Platinum()-crosslinked single-chain nanoparticles:an approach towards recyclable homogeneous catalysts[J]. Angewandte Chemie International Edition, 2017, 56(18):4950-4954. [57] WONG C M, MCBURNEY R T, BINDING S C, et al. Iridium(Ⅲ) homo-and heterogeneous catalysed hydrogen borrowing C-N bond formation[J]. Green Chemistry, 2017, 19(13):3142-3151. [58] AYRES J N, ASHFORD M W, STOCKL Y, et al. Deoxycyanamidation of alcohols with N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS)[J]. Organic Letters, 2017, 19(14):3835-3838. [59] STRENG E S, LEE D S, GEORGE M W, et al. Continuous N-alkylation reactions of amino alcohols using γ-Al2O3 and supercritical CO2:unexpected formation of cyclic ureas and urethanes by reaction with CO2[J]. Beilstein Journal of Organic Chemistry, 2017, 13:329-337. [60] 余秦伟, 李亚妮, 梅苏宁,等. 改性HZSM-5催化胺化异丙醇胺合成1,2-丙二胺[J]. 化工进展, 2014, 33(8):2060-2065. YU Q W, LI Y N, MEI S N, et al. Synthesis of 1,2-propanediamine by amination of isopropanolamine on modified HZSM-5[J]. Chemical Industry and Engineering Progress, 2014, 33(8):2060-2065. |
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