铑(III)催化的C(sp3)—H官能团化

doi:10.6023/cjoc202108012

摘要/Abstract

三价铑的外层电子为d⁶, 非常缺电子. 因此, Rh(III)催化C—H活化形成的C—Rh(III)键极性大,可以与多种包含极性键的试剂发生末端反应, 从而与钯等金属形成良好的交叉互补. 近年来, Rh(III)催化的C(sp²)—H键的官能团化反应取得了长足的发展, 在杂环骨架构建、药物修饰等方面应用越来越频繁. 惰性的C(sp³)—H键与C(sp²)—H键的活化机制类似,但是C(sp³)—H键的键能比C(sp²)—H键更强,并且没有易与金属中心发生轨道相互作用的π电子, 使该领域的探索和研究依然面临艰巨的挑战. 根据不同的反应类型进行分类, 系统地概括了Rh(III)催化C(sp³)—H键官能团化这一领域的研究进展.

关键词: 铑(III), C(sp³)—H官能团化, 烷基化, 芳基化, 羰基化, 烯基化, 胺化, 环化

The outer electron of trivalent rhodium is d⁶, which is very electron deficient. Therefore, the C—Rh(III) bond formed by Rh(III) catalyzed C—H activation is of big polarity and can react with a variety of terminal reagents containing polar bonds, thus forming a good cross complementarity with palladium and other metals. In recent years, significant progress has been made in the Rh(III) catalyzed C(sp²)—H bond functionalization. And many of the reported methods have been applied in heterocyclic skeleton construction and drug modification more and more frequently. Although the activation mechanism of inert C(sp³)—H bond is similar to that of C(sp²)—H bond, the bond energy of C(sp³)—H bond is more stronger, and there is no π electron easily to interact with the metal center, so the exploration and research in this field still face arduous challenges. The research progress in Rh(III) catalyzed C(sp³)—H functionalization is systematically summarized and the reported work is classified into different reaction types.

Key words: rhodium(III), C(sp³)—H functionalization, alkylation, arylation, carbonylation, alkenylation, amination, cyclization

引用此文

韩高旭, 许红涛, 侯卫. 铑(III)催化的C(sp³)—H官能团化[J]. 有机化学, 2022, 42(2): 391-423.

Gaoxu Han, Hongtao Xu, Wei Hou. Rhodium(III) Catalyzed C(sp³)—H Functionalization[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 391-423.

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图/表 49

图式1. Rh(III)催化C(sp3)—H键与重氮化合物的烷基化反应

Scheme 1. Rh(III)-catalyzed alkylation of C(sp3)—H bond with diazo compounds

图式2. Rh(III)催化8-甲基喹啉和马来酰亚胺的交叉偶联

Scheme 2. Rhodium(III)-catalyzed cross-coupling reaction of 8-methyquinolines and maleimides

图式3. Rh(III)催化8-甲基喹啉与3-丁烯-2-醇的反应

Scheme 3. Rhodium(III)-catalyzed reaction between 8-methylquinolines and but-3-en-2ol

图式4. Rh(III)催化8-甲基喹啉、烯烃与α,β-不饱和醛/酮的反应

Scheme 4. Rh(III)-catalyzed reaction of 8-methylquinoline or olefin with α,β-unsaturated aldehydes/ ketones

图式5. 钌(II)或铑(III)催化C(sp3)—H烷基化反应

Scheme 5. Ru(II) or Rh (III)-catalyzed C(sp3)—H alkylation

图式6. Rh(III)/手性羧酸催化8-乙基喹啉对映选择性C(sp3)— H烷基化

Scheme 6. Rhodium(III)/Chiral carboxylic acid catalyzed enantioselective C(sp3)—H alkylation of 8-ethylquinolines

图式7. Rh(III)催化8-甲基喹啉C(sp3)—H的甲基化

Scheme 7. Rhodium(III)-catalyzed C(sp3)—H methylation of 8-methylquinoline

图式8. Rh(III)催化C(sp3)—H键的芳基化

Scheme 8. Rh(III)-catalyzed arylation of C(sp3)—H bonds

图式9. Rh(III)催化8-甲基喹啉与有机基硼选择性单芳基化和二芳基化反应

Scheme 9. Rh(III)-catalyzed selective Mono- and Diarylation of 8-methylquinolines with organoborons

图式10. Rh(III)催化C(sp3)—H键β位或γ位的单芳基化反应

Scheme 10. Rh(III)-catalyzed monoarylation of β or γ C(sp3)—H Bonds

图式11. Rh(III)催化烯烃和芳基硼试剂的烯丙基-芳基偶联反应

Scheme 11. Rh(III)-catalyzed ally-aryl coupling of olefins and arylboron reagents

图式12. 烯丙基C(sp3)—H键非导向去氢偶联的芳基化

Scheme 12. Non-directed cross-dehydrogenative arylation of allylic C(sp3)—H bonds

图式13. Rh(III)催化8-甲基/甲酰基喹啉与重氮化合物直接芳基化

Scheme 13. Rh(III)-catalyzed straightforward arylation of 8-methy/formylquinolines with diazo compounds

图式14. Rh(III)催化C(sp3)—H和C(sp2)—H键羰基化

Scheme 14. Rh(III)-catalyzed acylation of C(sp3)—H and C(sp2)—H Bonds

图式15. Rh(III)催化C(sp3)—H键与环丙烯酮的酰化反应

Scheme 15. Rh(III)-catalyzed acylation of C(sp3)—H bonds with cyclopropenones

图式16. Rh(III)催化C(sp3)—H键与异氰酸酯的氨羰基化反应

Scheme 16. Rh(III)-catalyzed C(sp3)—H bonds aminocarbonylation with isocyanates

图式17. 快速微波辅助, 非溶剂条件下通过Rh(III)催化C(sp3)—H活化实现8-甲基喹啉的官能团化

Scheme 17. Rapid microwave-assisted, solvent-free approach to functionalization of 8-methylquinolines via Rh(III)-catalyzed C(sp3)—H activation

图式18. Rh(III)催化8-甲基喹啉C(sp3)—H活化与炔烃的烯基化反应

Scheme 18. Rh(III)-catalyzed alkenylation reaction of 8-methylquinolines with alkynes by C(sp3)—H activation

图式19. Rh(III)催化N-烷基-1H-吡唑烯烃化

Scheme 19. Rh(III)-catalyzed alkenylation of N-alkyl-1H- pyrazoles

图式20. Rh(III)催化8-甲基喹啉苄基位的α-氟的烯化反应

Scheme 20. Rh(III)-catalyzed benzylic α-fluoroalkenylation of 8-methylquinolines

图式21. Rh(III)催化8-甲基喹啉与醌、噻吩的C(sp3)—H烯基化和芳基化反应

Scheme 21. Rh(III)-catalyzed C(sp3)—H alkenylation and arylation of 8-methylquinolines with quinones and thiophenes

图式22. Rh(III)催化8-甲基喹啉与马来酰亚胺的偶联

Scheme 22. Rh(III)-catalyzed coupling of 8-methylquinolines with maleimides

图式23. Rh(III)催化碳氢底物和碘叶立德试剂偶联

Scheme 23. Rh(III)-catalyzed coupling of C—H substrates with iodonium ylides

图式24. Rh(III)催化8-甲基喹啉与叠氮化物的酰胺化反应

Scheme 24. Rh(III)-catalyzed amidation of 8-methylquinolines with azides

图式25. Rh(III)催化氨基苯碘酮导向胺化反应

Scheme 25. Rh(III)-catalyzed direct amination with amidobenziodoxolones

图式26. Rh(III)催化C(sp2)—H或C(sp3)—H键的胺化

Scheme 26. Rh(III)-catalyzed amination of C(sp2)—H or C(sp3)—H bonds

图式27. Rh(III)催化8-甲基喹啉与偶氮二甲酸酯的C(sp3)—H胺化反应

Scheme 27. Rh(III)-catalyzed C(sp3)—H amination of 8- methylquinolines with azodicarboxylates

图式28. Rh(III)催化C(sp3)—H键的胺化

Scheme 28. Rh(III)-catalyzed amination of C(sp3)—H bonds

图式29. Rh(III)催化烯丙基C—H键胺化反应

图式30. Rh(Ⅲ)催化3, 5-二甲基吡唑导向次级C(sp3)—H键的胺化反应

Scheme 30. Rh(Ⅲ)-catalyzed secondary C(sp3)—H bonds amidation directed by 3,5-dimethylpyrazole

图式31. 二硫杂环导向Rh(III)催化C(sp3)—H键酰胺化

Scheme 31. Dithiane-directed Rh(III)-catalyzed amidation of C(sp3)—H bond

图式32. Rh(III)和Ir(III)催化烯丙基C(sp3)—H键的胺化反应

Scheme 32. Rh(III) and Ir(III)-catalyzed amination reactions of allylic C(sp3)—H bonds

图式33. Rh(III)催化C(sp3)—H键的胺化

Scheme 33. Rh(III)-catalyzed amination of C(sp3)—H bonds

图式34. Cp*RhIII/手性羧酸催化8-烷基喹啉的对映选择性亚甲基C(sp3)—H酰胺化反应

Scheme 34. Cp*RhIII/chiral carboxylic acid system catalyzed enantioselective methylene C(sp3)—H amidation of 8-alkylquinolines

图式35. 区域和对映选择性烯丙基C—H酰胺化的平面手性铑吲哚催化剂的设计

Scheme 35. Designing a planar chiral rhodium indenyl catalyst for regio- and enantioselective allylic C—H amidation

图式36. Rh(III)催化吡咯的合成

Scheme 36. Rh(III)-catalyzed the synthesis of pyrrole

图式37. Rh(Ⅲ)催化分子内烯丙基胺化反应

Scheme 37. Rh(III)-catalyzed intramolecular allylic amination

图式38. Rh(Ⅲ)催化级联氧化环化反应

Scheme 38. Rh(III)-catalyzed cascade oxidative annulation

图式39. Rh(III)催化不饱和磺酰胺和炔烃的反应

Scheme 39. Rh(III)-catalyzed the reaction of unsaturated sulfonamides with alkynes

图式40. Rh(III)催化氧化环加成合成吡咯

Scheme 40. Rh(III)-catalyzed oxidative cycloaddition for the synthesis of pyrroles

图式41. Rh(III)催化烯烃的烯丙基碳氢活化并与邻炔基苯胺的偶联

Scheme 41. Rh(III)-catalyzed allylic C—H activation of olefins and coupling with o-alkynylanilines

图式42. Rh(III)催化芳胺氮氧化物与重氮化合物的碳氢官能团化

Scheme 42. Rh(III)-catalyzed C-H functionalization of arylamine N-Oxides with diazo compounds

图式43. Rh(III)催化α-烷氧基γ-内酰胺类化合物的合成

Scheme 43. Rh(III)-catalyzed the synthesis of α-alkoxylated γ-lactams compounds

图式44. Rh(III)催化聚烯烃均相硼化反应

Scheme 44. Rh(III)-catalyzed homogeneous borylation of polyolefin

图式45. Rh(III)催化聚丙烯的官能团化

Scheme 45. Rh(III)-catalyzed the functionalization of polypropylene

图式46. Rh(III)催化吲哚核的硫基化

Scheme 46. Rh(III)-catalyzed thiolation of indole core

图47. Rh(III)催化醇和烯烃的烯丙基C—H醚化反应

Figure 47. Rh(III)-catalyzed allylic C—H etherification of olefins with alcohols

图48. Rh(III)催化8-甲基喹啉的C(sp3)—H乙酰氧基化反应

Figure 48. Rh(III)-catalyzed C(sp3)—H acetoxylation of 8- methylquinolines

图49. Rh(III)催化烯丙基位的炔化反应

Figure 49. Rh(III)-catalyzed alkynylation of allylic

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铑(III)催化的C(sp³)—H官能团化

Rhodium(III) Catalyzed C(sp³)—H Functionalization

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