羰基化反应在大宗化学品以及精细化学品合成中的应用

doi:10.6023/cjoc202301025

摘要/Abstract

简单的有机化合物如不饱和烃、卤代烃等与一氧化碳反应合成含羰基官能团化学品的羰基化反应因具有原子经济性、对环境友好及化学/区域选择性高等优点而备受关注. 综述了近几年通过发展新催化剂体系催化羰基化反应合成具有工业应用前景的大宗化学品和精细化学品的研究进展, 包括氢甲酰化反应合成醛, 氢酯化反应合成酯, 氢酰胺化反应合成酰胺, “氢甲酰化-氢化”串联反应合成醇, 以及合成酸酐、酮、酰卤等高附加值产品. 最后, 对羰基化反应在合成大宗化学品以及精细化学品中的发展前景以及存在难点进行展望, 以期发展更多类型的羰基化反应为其工业化应用提供参考.

关键词: 羰基化反应, 一氧化碳, 大宗化学品, 精细有机化学品, 烯烃, 氢甲酰化

The reaction between unsaturated/halogenated hydrocarbons and carbon monoxide to construct chemicals containing carbonyl modules has attracted much attention due to its advantages, such as atomic economy, environmental friendliness and high chemical/regional selectivity. The research progress in the synthesis of bulk and fine chemicals with industrial application prospects through the construction of new catalytic systems for carbonylation in recent years is summarized, including the synthesis of aldehydes through hydroformylation, esters through hydroesterification, amides through aminocarbonylation, alcohols through “hydroformylation hydrogenation” tandem reaction, as well as the synthesis of high value-added products such as acid anhydrides, ketones, and acyl halides. Finally, the development prospects and existing difficulties of carbonylation are discussed, hoping to provide reference for promoting the industrial application of carbonylation reactions.

Key words: carbonylation, carbon monoxide, bulk chemical, fine organic chemical, olefin, hydroformylation

引用此文

史会兵, 王耀伟, 王鹏, 赵德明, 冯保林, 晏耀宗, 杨桂爱. 羰基化反应在大宗化学品以及精细化学品合成中的应用[J]. 有机化学, 2024, 44(6): 1811-1830.

Huibing Shi, Yaowei Wang, Peng Wang, Deming Zhao, Baolin Feng, Yaozong Yan, Guiai Yang. Application of Carbonylation in the Synthesis of Bulk and Fine Chemicals[J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1811-1830.

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图/表 38

图式1. 羰基化反应在合成高附加值化学品中的应用

Scheme 1. Application of carbonylation in the synthesis of high value-added chemicals

图式2. 铑单原子催化剂催化烯烃高区域选择性氢甲酰化

Scheme 2. Rh single-atom as highly regioselective catalyst for hydroformylation of olefins

图式3. 铑催化环丙基三取代烯烃的化学、区域和对映选择性氢甲酰化反应

Scheme 3. Rhodium-catalyzed chemo-, regio- and enantioselective hydroformylation of cyclopropyl-functionalized trisubstituted alkenes

图式4. 温和条件下未修饰的羰基钴催化的氢甲酰化反应

Scheme 4. Hydroformylation catalyzed by unmodified cobalt carbonyl under mild conditions

图式5. 铑催化非活化烷基氯代物的甲酰化反应

Scheme 5. Rhodium-catalyzed formylation of unactivated alkyl chlorides

图式6. Et3N作为添加剂调控[Rh(cod)Cl]2/PPh3催化烯烃高选择性、可循环的均相氢甲酰化反应

Scheme 6. [Rh(cod)Cl]2/PPh3 catalyzed highly selective and recyclable homogeneous hydroformylation of olefins regulated by Et3N as additive

图式7. 钯催化1,3-二烯羰基化直接合成己二酸酯

Scheme 7. Direct synthesis of adipic acid esters via palladium-catalyzed carbonylation of 1,3-dienes

图式8. 钯催化乙烯基芳烃不对称Markovnikov氢羧化反应和氢酯化反应合成2-芳基丙酸以及2-芳基丙酸酯

Scheme 8. Palladium-catalyzed asymmetric Markovnikov hydroxycarbonylation and hydroalkoxycarbonylation of vinyl arenes to synthesize 2-arylpropanoic acids and esters

图式9. 镍催化环丙烯的不对称氢芳氧羰基化和氢烷氧羰基化反应

Scheme 9. Nickel-catalyzed asymmetric hydroaryloxy- and hydroalkoxy-carbonylation of cyclopropenes

图式10. 双功能配体调控钯催化脂肪族烯烃的氢酯化反应

Scheme 10. Bifunctional ligand regulated palladium-catalyzed selective hydroesterification of aliphatic alkenes

图式11. 铁催化双电子转移过程的烷基溴烷氧羰基化反应

Scheme 11. Iron-catalyzed alkoxycarbonylation of alkyl bromides via a two-electron transfer process

图式12. 锰催化烷基氯的烷氧羰基化反应

Scheme 12. Manganese-catalyzed alkoxycarbonylation of alkyl chlorides

图式13. 温和条件下烯烃的高选择性反Markovnikov氢酯化反应

Scheme 13. Highly selective anti-Markovnikov hydroesterification of alkenes under mild conditions

图式14. 钯催化烯烃羰基化高区域选择性合成线性和支链硒酸酯

Scheme 14. Pd catalyzed high regioselective carbonylation of alkenes to synthesize linear and branched selenoesters

图式15. 钯催化1,1-二取代和1,1,2-三取代烯烃的Markovnikov氢氨羰基化反应合成含有季碳中心的酰胺

Scheme 15. Palladium-catalyzed Markovnikov hydroaminocarbonylation of 1,1-disubstituted and 1,1,2-trisubstituted alkenes for formation of amides with quaternary carbon

图式16. 可溶性多相钯催化烯烃和炔烃的高效Markovnikov羰化胺化反应

Scheme 16. Highly efficient Markovnikov hydroaminocarbonylation of alkenes and alkynes catalyzed by a “soluble” heterogeneous Pd catalyst

图式17. 烯烃与芳香胺的反Markovnikov羰化胺化反应

Scheme 17. Anti-Markovnikov hydroaminocarbonylation of alkenes with aromatic amines

图式18. 铜催化烷基卤代物的羰基化合成α-酮基酰胺和烷基卤化物酰胺

Scheme 18. Copper-catalyzed carbonylation of alkyl halides to synthesize α-keto amides and alkyl halide amides

图式19. 光诱导烯烃的五组分自由基三氟甲基化羰基化胺化串联反应

Scheme 19. Photoinduced five-component radical relay CF3-aminocarbonylation of alkenes

图式20. 钯催化烷基芳烃和醛亚胺之间的羰基化合成β-内酰胺

Scheme 20. Palladium catalyzed carbonylation between alkyl aromatic hydrocarbons and aldehyde imines to synthesize β-lactams

图式21. 钯催化羰基化合成二酰胺和酰胺基酯

Scheme 21. Synthesis of diamides and amido-esters via Pd- catalyzed carbonylation.

图式22. 可见光驱动的钴催化还原氢甲酰化反应合成醇

Scheme 22. Synthesis of alcohol by cobalt-catalyzed visible- light-driven reductive hydroformylation

图式23. 酸促进“钌-钴”双催化剂体系用于CO2和烯烃的氢甲酰化合成醇

Scheme 23. Acid-promoted hydroformylative synthesis of alcohol with CO2 by ruthenium-cobalt dual catalytic system

图式24. 脂肪酸的C—H键活化羰基化反应合成环酸酐

Scheme 24. Synthesis of cyclic anhydrides via carbonylation of C—H bond activation of aliphatic acids

图式25. 镍催化的酯类化合物羰基化反应

Scheme 25. Nickel-catalyzed carbonylation of esters

图式26. 光介导铜催化烷基卤化物的羰基化反应合成脂肪酸酐

Scheme 26. Light-mediated synthesis of aliphatic anhydrides by Cu-catalyzed carbonylation of alkyl halides

图式27. 邻碘苯胺与烯烃的对映选择性羰化Heck偶联反应

Scheme 27. Enantioselective carbonylative Heck coupling reaction of o-iodoanilines with allenes

图式28. 镍催化烯丙醇和有机烷烃的羰基化偶联反应

Scheme 28. Carbonylative coupling reaction of allylic alcohols and organoalanes catalyzed by Ni catalysis

图式29. 镍催化不饱和烃与有机锌试剂、CO的酰基锌化反应

Scheme 29. Nickel-catalyzed acylzincation of unsaturated hydrocarbons with organozincs and CO

图式30. 芳烃通过C(sp2)—H的位点选择性羰基化直接合成1,2-二芳基乙酮

Scheme 30. Site-selective carbonylation of arenes via C(sp2)—H thianthrenation to access 1,2-diarylethanones

图式31. 可见光/钯协同催化酰基氟化物的合成

Scheme 31. Synthesis of acyl fluorides catalyzed by visible light/palladium synergy

图式32. 一种双功能光驱动钯催化剂: 打破羰基化反应的障碍

Scheme 32. A dual light-driven palladium catalyst: breaking the barriers in carbonylation reactions

图式33. 可见光驱动镍催化烷基卤化物羰基化合成酰氯

Scheme 33. A visible light driven Ni catalyzed carbonylation to synthesize acid chlorides from alkyl halides

图式34. 钯催化烯烃区域选择性氢氯羰基化生成酰氯化合物

Scheme 34. Palladium-catalyzed regiodivergent hydrochlorocarbonylation of alkenes for formation of acid chlorides

图式35. 铜催化烷基卤化物的羰基化硅烷化反应合成酰基硅烷

Scheme 35. Cu-catalyzed carbonylative silylation of alkyl halides to synthesize acylsilanes

图式36. β-羰基辅助烯烃的不对称烷氧基和羟基羰基化反应

Scheme 36. Asymmetric alkoxy- and hydroxy-carbonylations of alkenes assisted by β-carbonyl groups

图式37. 数据科学支持钯催化磺酰亚胺对映选择性芳基羰基化

Scheme 37. Data science-enabled Pd catalyzed enantioselective aryl-carbonylation of sulfonimidamides

图式38. 钴催化烯烃多组分羰基化反应高效合成β-全氟烷基亚胺、酰胺和酯

Scheme 38. Cobalt-catalyzed multicomponent carbonylation of olefins for efficient synthesis of β-perfluoroalkyl imides, amides, and esters

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