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

doi:10.6023/cjoc202108012

Abstract

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

Cite this article

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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Fig. & Tab. 49

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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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铑(III)催化的C(sp3)—H官能团化