配体在Cp*Rh(III)催化C—H键官能团化反应中的应用

doi:10.6023/cjoc202211039

摘要/Abstract

Cp*Rh(III)催化剂因其优异的催化活性、稳定性以及反应条件温和性, 在惰性C—H键官能团化领域有着广泛的应用. 然而, 由于Rh(III)配位轨道数量的限制, 针对Cp*Rh(III)催化体系的外加配体研究相对较少. 近年来, 本课题组致力于通过外加配体来促进Cp*Rh(III)对C—H键的官能团化, 并进一步对产物的选择性进行调控. 系统地总结了由配体促进的Cp*Rh(III)催化C—H键官能团化反应的相关工作, 包括非手性活化和手性活化, 概述了配体在催化体系中所起到的作用, 并对部分反应机理进行了简要描述.

关键词: Cp*Rh(III), C—H键官能团化, 配体

Cp*Rh(III) catalysts have shown excellent performance in the field of inert C—H bond functionalization because of their high activity and stability under mild conditions. However, limited by the number of Rh(III) coordination orbitals, the ligand studies in Cp*Rh(III) catalytic system are relatively few. Recently, our research group has been focusing on the external ligands promoted C—H bond functionalization with high activity and selectivity. In this review, the related works of Cp*Rh(III) catalyzed C—H bond functionalization are systematically summarized, including both symmetric and asymmetric C—H activation, the role of ligands in the Cp*Rh(III) catalytic system is discussed, and some reaction mechanisms are briefly described.

Key words: Cp*Rh(III), C—H bond functionalization, ligands

引用此文

潘彦年, 秦萧, 袁成凯, 鲁艺. 配体在Cp*Rh(III)催化C—H键官能团化反应中的应用[J]. 有机化学, 2023, 43(3): 924-948.

Yannian Pan, Xiao Qin, Chengkai Yuan, Yi Lu. Application of Ligands in Cp*Rh(III)-Catalyzed C—H Bond Functionalization Reaction[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 924-948.

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图/表 34

图式1. Cp*Rh(III)催化的C—H键官能团化反应

Scheme 1. Cp*Rh(III)-catalyzed C—H bond functionalization

图式2. Rh(III)催化苯甲酰胺邻位C(sp2)—H键的烯基化反应

Scheme 2. Rh(III)-catalyzed alkenylation reaction of benzamide ortho-position C(sp2)—H bond

图式3. Rh(III)活化醛基C(sp2)—H键的Heck反应

Scheme 3. Rh(III)-catalyzed Heck reaction of aldehyde C(sp2)—H bond

图式4. Cp*Rh(III)催化C(sp2)—H键与烯烃的氧化偶联反应

Scheme 4. Cp*Rh(III)-catalyzed oxidative coupling reaction of C(sp2)—H bond with alkenes

图式5. 温和条件下Rh(III)催化三次连续的C—H键官能团化反应

Scheme 5. Rh(III)-catalyzed three-step consecutive C—H functionalization under mild condition

图式6. 克级反应和反应机理

Scheme 6. Gram scale synthesis and proposed reaction mechanism

图式7. [Cp*RhCl2]2催化苯基吡唑与内炔烃的氧化偶联反应

Scheme 7. [Cp*RhCl2]2-catalyzed oxidative coupling reaction of phenylpyrazoles and internal alkynes

图式8. 温和条件下N-五氟苯基苯甲酰胺的炔基化反应

Scheme 8. Alkynylation of N-pentafluorophenyl benzoamides under mild condition

图式9. Rh(III)催化的酮亚胺和二苯乙炔的[3+2]环化反应

Scheme 9. Rh(III)-catalyzed [3+2] cyclization of ketoimides and diphenylacetylenes

图式10. Rh(III)催化芳烃与苯硼酸频哪醇酯的C—H键芳基化反应

Scheme 10. Rh(III)-catalyzed C—H arylation reaction of arenes and ArBpin

图式11. Rh(III)催化三甲基吡唑导向的β位或γ位C(sp3)—H键芳基化反应

Scheme 11. Rh(III)-catalyzed β- or γ-C(sp3)—H arylation reaction directed by trimethylpyrazole

图式12. Rh(III)催化的8-甲基喹啉与有机硼试剂选择性单芳基化和二芳基化

Scheme 12. Rh(III)-catalyzed selective mono- and diarylation of 8-methylquinolines with organoborons

图式13. Rh(III)催化喹啉氮氧化物C(8)位的C—C键偶联反应

Scheme 13. Rh(III)-catalyzed C—C bond formation of quinoline N?oxides at the C(8) position

图式14. Cp*Rh(III)催化2-苯胺基嘧啶和2-苯氧基嘧啶与α-重氮酯的烷基化反应

Scheme 14. Cp*Rh(III)-catalyzed alkylation of 2-anilinopyrimidines and 2-phenoxypyrimidines with α-diazo esters

图式15. Cp*Rh(III)催化醌类重氮化合物与2-吡啶酮C(6)位选择性芳基化反应

Scheme 15. Cp*Rh(III)-catalyzed C(6)-selective arylation of 2?pyridones with quinone diazides

图式16. Rh(III)催化8-甲基喹啉和8-甲酰喹啉与重氮化合物发生的芳基化反应

Scheme 16. Rh(III)-catalyzed arylation of 8-methy/formylquinolines with diazo compounds

图式17. Rh(III)催化酰肼导向的C(sp2)—H胺化反应

Scheme 17. Rh(III)-catalyzed hydrazine-directed C(sp2)—H amination

图式18. Rh(III)催化弱导向酰胺底物与游离的仲胺和苯胺发生的胺化反应

Scheme 18. Rh(III)-catalyzed amination of weakly-directing amide substrates with free secondary amines and anilines

图式19. Rh(III)催化的由MPAAs促进的sp2硫化反应

Scheme 19. Rh(III)-catalyzed sp2 thiolation promoted by MPAAs

图式20. 硫化反应机理

Scheme 20. Thiolation reaction mechanism

图式21. Rh(III)催化的硫缩醛导向的C(sp3)—H酰胺化反应

Scheme 21. Rh(III)-catalyzed thioacetal-directed C(sp3)—H amidation

图式22. Rh(III)催化羰基弱导向的C(sp3)—H键酰胺化反应

Scheme 22. Rh(III)-catalyzed carbonyl-directed C(sp3)—H bond amidation

图式23. Rh(III)催化C(sp2)—H键对碳氮双键和碳氧双键的加成反应

Scheme 23. Rh(III)-catalyzed C(sp2)—H addition to C=N and C=O

图式24. Rh(III)催化8-甲基喹啉C(sp3)—H键的酰基化反应

Scheme 24. Rh(III)-catalyzed C(sp3)—H bond acylation of 8-methylquinolines

图式25. RhCl3?3H2O催化的C(sp2)—H键的直接羧基化反应

Scheme 25. RhCl3?3H2O-catalyzed C(sp2)—H bond direct carboxylation

图式26. 手性Cp控制C—H键官能团化生成对映选择性产物

Scheme 26. C—H bond enantioselective functionalization controlled by chiral Cp

图式27. CCA促进的二芳基甲胺与重氮丙二酸二甲酯发生的不对称烷基化反应

Scheme 27. CCA-enabled asymmetric alkylation of diarylmethylamines with dimethyl diazomalonates

图式28. CCA促进的8-烷基喹啉苄位亚甲基的对映选择性酰胺化反应

Scheme 28. CCA-enabled enantioselective amideation of benzyl methylene of 8-alkyl quinolones

图式29. CCA促进的C(sp3)—H活化形成对映选择性的C—C键

Scheme 29. CCA-enabled C(sp3)—H activation to form enantioselective C—C bond

图式30. CCA促进的2-烷基吡啶与二噁唑酮的不对称酰胺化

Scheme 30. CCA-enabled asymmetric amidation of 2-alkyl pyridines with dioxazoldones

图式31. 手性CpRh(III)配合手性羧酸催化N-磺酰亚胺与炔烃发生的不对称[3+2]环化反应

Scheme 31. Chiral CpRh(III) coordinates with CCA to catalyze the asymmetric [3+2] annulation of N-sulfonyl ketimines and alkynes

图式32. 手性CpRh(III)配合手性羧酸催化二芳基亚砜亚胺与重氮化合物反应

Scheme 32. Chiral CpRh(III) coordinates with CCA to catalyze the reaction of diaryl sulfoximines with diazo compounds

图式33. 手性CpRh(III)配合手性羧酸催化1-芳基异喹啉衍生物与富电子杂环芳烃的交叉偶联反应

Scheme 33. Chiral CpRh(III) coordinates with CCA to catalyze cross-coupling reaction of 1?aryl isoquinoline derivatives with electron-rich heteroarenes

图式34. 手性CpRh(III)配合手性羧酸催化1-芳基异喹啉衍生物和炔烃之间的直接环化反应

Scheme 34. Chiral CpRh(III) coordinates with CCA to catalyze the direct annulation reactions between 1-aryl isoquinoline derivatives and alkynes

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