Alternative Strategies Enabling Cross-Dehydrogenative Coupling: Access to C—C Bonds

doi:10.6023/cjoc202009053

Abstract

Cross-dehydrogenative coupling (CDC) reactions have been esteemed as one of the straightforward and efficient tool for C—C bond formation. Typically, these reactions are generally realized via solvent-based thermochemistry, using a round bottom flask and a magnetic or mechanical stirrer. With the development of new synthetic strategies, alternative technologies currently available in laboratories that facilitate CDC reactions, such as photochemistry, electrochemistry and mechanochemistry have arisen rapidly, providing green and high efficiency strategies for the construction of C—C bonds which are perfect complement to traditional thermochemistry. In order to compare the advantages of each approaches more clearly, and promote the development of CDC reactions, CDC reactions related to two or more enabling technologies of same or similar substrates are reviewed, hoping to provide help for the development of CDC reaction and the development of new organic synthesis methods.

Key words: cross-dehydrogenative coupling, thermochemistry, photochemistry, electrochemistry, mechanochemistry

Cite this article

Hao Wang, Ping Ying, Jingbo Yu, Weike Su. Alternative Strategies Enabling Cross-Dehydrogenative Coupling: Access to C—C Bonds[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1897-1924.

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Fig. & Tab. 45

Scheme 1. Alternative strategies access to C—C bond via CDC reactions

Scheme 2. CDC reactions for C(sp3)—H electrophilic substrates

Scheme 3. CDC reactions of tetrahydroisoquinolines with nitromethane (MM=mix miller)

Scheme 4. Proposed mechanism for CDC reaction of tetrahydroisoquinoline and nitromethane under photocatalysis

Scheme 5. CDC reactions of tetrahydroisoquinolines with ketones

Scheme 6. Proposed mechanism for CDC reaction of tetrahydroisoquinolines and ketones catalyzed by synergetic vanadium- and organocatalysis (L=acetyl acetonate)

Scheme 7. Asymmetric CDC reactions of tetrahydroisoquinolines with aldehydes and ketones

Scheme 8. Substrates scope of asymmetric CDC reactions of N-carbamoyl tetrahydroisoquinolines with aldehydes

Scheme 9. Proposed mechanism for asymmetric CDC reactions of tetrahydroisoquinolines with ketones

Scheme 10. Proposed mechanism for the formation of imine promoted by Ru/Co cocatalysis under visible light irradiation

Scheme 11. CDC reactions of tetrahydroisoquinolines and analogues with acidic methylenes

Scheme 12. CDC reactions of glycine ester with β-ketoesters

Scheme 13. CDC reactions of 3-benzylic indoles with 1,3-dicarbonyls

Scheme 14. Plausible asymmetric CDC reaction mechanism by liquid-assisted grinding between 3-benzylic indoles and 1,3-dicarbonyls

Scheme 15. Asymmetric CDC reactions of xanthenes with aldehydes

Scheme 16. Prosposed mechanism for asymmetric CDC reactions of xanthenes with aldehydes by electrocatalysis

Scheme 17. Selected examples of asymmetric CDC reactions of xanthenes with aldehydes by photoocatalysis

Scheme 18. CDC reactions of tetrahydroisoquinolines with indoles (MM=mix miller)

Scheme 19. CDC reactions of tetrahydroisoquinolines with azoles

Scheme 20. Selected examples for CDC reactions of tetrahydroisoquinolines with azoles catalyzed by photocatalysis

Scheme 21. CDC reactions of glycine derivatives with indoles

Scheme 22. Reactions of α-substituted glycine derivatives with indoles

Scheme 23. Proposed mechanism for CDC reaction of α-substituted glycine derivatives with indoles by external heating/stirring

Scheme 24. Proposed mechanism for asymmetric Friedel-Crafts reaction of α-substituted glycine derivatives with indoles by photocatalysis

Scheme 25. CDC reactions of glycine derivatives with phenols and naphthols

Scheme 26. Selected examples for CDC reactions of glycine derivatives with phenols

Scheme 27. CDC reactions of glycine derivatives with azoles

Scheme 28. CDC reactions of glycine derivatives with N-sub- stituted anilines

Scheme 29. CDC reactions of cyclo(hetero)alkanes with azoles

Scheme 30. Proposed mechanism for CDC reaction of cyclic ethers with azoles under external heating/stirring

Scheme 31. Proposed mechanism for CDC reaction of N-Boc-pyrrolidine with azoles under visible light irradiation

Scheme 32. Substrate scope for CDC reaction of N-Boc-pyrrolidine and azoles and the modification of drug structure

Scheme 33. CDC reactions of quinoxalin-2(1H)-ones with ethers

Scheme 34. CDC reactions of tetrahydroisoquionolines with alkynes

Scheme 35. Selected examples of asymmetric CDC reaction of tetrahydroisoquionolines with alkynes by Fe/Zn catalysis

Scheme 36. Proposed mechanism for asymmetric CDC reaction of tetrahydroisoquionolines with alkynes catalyzed by Fe/Zn catalysis

Scheme 37. CDC reactions of phenols with arenes

Scheme 38. Proposed mechanism for CDC reaction of phenol with arene by electrocatalysis

Scheme 39. Substrate scope for CDC reactions of phenol with arene by photocatalysis

Scheme 40. CDC reactions of two anilines

Scheme 41. CDC reactions for functional modification of drug molecules by electrocatalysis

Scheme 42. CDC reactions of phenols with anilines

Scheme 43. Intramolecular CDC reactions of N-aryl enamines

Scheme 44. CDC reactions of isoquinolines with aldehydes

Scheme 45. Alkaloids synthesis by CDC reaction of isoquinolines with aldehydes

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