过渡金属催化氯代物的羰基化反应研究进展

doi:10.16085/j.issn.1000-6613.2022-1859

摘要/Abstract

摘要：

有机氯代物相对于溴代物和碘代物价格低廉且储量丰富，其通过羰基化反应合成的下游产品醛、羧酸、酰胺、酯在大宗化学品、精细化学品以及医药中间体等的生产上有重要应用。本文综合评述了氯代物羰基化反应合成高附加值化学品的重要性, 介绍了几种不同类型的氯代物（芳基氯代物、烯丙基氯代物、苄基氯代物、α-氯代酮、1,1-二氯-1-乙烯基化合物、烷基氯代物）羰基化反应（甲酰化反应、酯化反应、酰胺化反应和羧化反应等）在发展新型催化剂体系及高效合成目标产物方面的研究进展, 并对该类底物羰基化反应存在的难点以及未来发展方向进行了展望。未来发现更多类型的反应和催化剂体系，实现氯代物的温和羰基化是有机化学研究以及工业化生产的难题及热点。

关键词: 氯代物, 羰基化反应, 一氧化碳, 催化剂, 有机化合物

Abstract:

Compared with brominated and iodinated substitutes, chlorinated substitutes are cheaper and more abundant in reserves. The downstream products such as aldehydes, carboxylic acids, amides and esters synthesized by carbonylation reaction have important applications in the production of bulk chemicals, fine chemicals and pharmaceutical intermediates. This paper comprehensively reviews the importance of chlorinated compounds carbonylation to synthesize high value-added chemicals, and introduces the research progress of several different types of chlorinated compounds (aryl chlorinated compounds, allyl chlorinated compounds, benzyl chlorinated compounds, α-chlorinated ketones, 1,1-dichloro-1-vinyl compounds, alkyl chlorides) and their carbonylation reactions (formylation, esterification, amination, carboxylation, etc.) in the development of new catalyst systems and efficient synthesis of target products. The difficulties and future development of carbonylation of such substrates are also prospected. In the future, the development of more types of reactions and catalyst systems that accomplish the mild carbonylation of chlorinated compounds would be a hot spot in organic chemistry research and industrial production.

Key words: chlorinated compounds, carbonylation, carbon monoxide, catalyst, organic compounds

中图分类号:

O643.32

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.

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.

图/表 15

图1 有机氯代物的羰基化反应转化

图2 钯催化芳基氯代物与亲核试剂羰基化反应机理

图3 芳基氯化物羰化酯化反应的高效催化剂

图4 钯配合物催化烯丙基氯化物的羰基化和双羰基化反应

图5 钯催化烯丙基氯羰基化制备β,γ-不饱和酯/酰胺

图6 苄基氯化物与末端炔烃的羰基化偶联反应

图7 钯催化苄基氯代物的高效羰化胺化反应

图8 以卤化苄为底物合成杂环化合物3,4-二芳基β-内酰胺以及色甲酮

图9 两相体系中钯催化氯化苄羰基化反应

图10 钯催化苄基氯代物羰化酯化反应合成苯乙酸

图11 温和条件下苄基氯的羰化酯化反应

图12 钯催化的α-氯酮参与的羰化串联反应

图13 α-氯酮的羰基化/迈克尔加成串联反应

图14 非贵金属催化剂催化氯代烷烃与CO的光催化羰基化反应

图15 铑催化非活化烷基氯代物的羰化酯化反应

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