Advances in Radical Mediated 1,2-Aryl Migration Reactions of α,α-Diarylallyl Alcohols

doi:10.6023/cjoc202208028

Abstract

As widely used building blocks, allyl alcohols can directly participate in the synthesis reaction without pre-functionalization. In recent years, the migration reaction of allyl alcohols has received great attention, and such reactions are often realized by semipinacol or neophyl rearrangement, providing a powerful strategy for the synthesis of various important carbonyl compounds. The latest progress of radical-initiated group migration reactions involving diaryl allyl alcohols as synthons systematically is reviewed, the scope, limitations and some mechanisms of the reaction are discussed, and the challenges and future development trends in this field are prospected.

Key words: allyl alcohols, migration reaction, semipinacol, neophyl rearrangement, carbonyl compounds

Cite this article

Jiantao Zhang, Yawen Deng, Nuolin Mo, Lianfen Chen. Advances in Radical Mediated 1,2-Aryl Migration Reactions of α,α-Diarylallyl Alcohols[J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 426-435.

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Fig. & Tab. 39

Scheme 1. Radical-mediated 1,2-migration of allyl alcohols

Scheme 2. Possible mechanism of trifluoromethylation of allyl alcohols

Scheme 3. Metal-catalyzed trifluoromethylation of allyl alcohols

Scheme 4. Metal-free trifluoromethylation of allyl alcohols

Scheme 5. Visible-light-enabled trifluoromethylation of allyl alcohols

Scheme 6. Visible-light-induced trifluoromethylation of allyl alcohols

Scheme 7. Electrochemical oxidative trifluoromethylation of allyl alcohols

Scheme 8. Cu-catalyzed perfluoroalkylation of allyl alcohols

Scheme 9. AgSCF3-mediated trifluoromethylthiolation of allyl alcohol

Scheme 10. Possible mechanism of cyanoalkylation of allyl alcohols

Scheme 11. Cu-catalyzed cyanoalkylation of allyl alcohols with alkyl nitriles

Scheme 12. TBPB-mediated of allyl alcohols with acetonitrile

Scheme 13. Visible-light-induced cyanoalkylation of allyl alcohols with alkyl nitriles

Scheme 14. Possible mechanism of acylation of allyl alcohols

Scheme 15. UV light-mediated aroylation of allyl alcohols with prop-2-en-1-ols

Scheme 16. Oxidative acylation of allyl alcohols with aryl aldehydes

Scheme 17. Photocatalytic radical aroylation of unactivated alkenes

Scheme 18. Radical 1,2-alkylarylation/acylarylation of allyl alcohols with aldehydes

Scheme 19. TBPB-promoted radical alkylation reaction of allyl alcohols with ethers

Scheme 20. DTBP-promoted radical alkylation reaction of allyl alcohols with alkanes

Scheme 21. Possible mechanism of alkylation of allyl alcohols

Scheme 22. Ni-mediated alkanamidation of allyl alcohols with amides

Scheme 23. Visible-light-enabled oxidative alkylation of allyl alcohols with dimethyl sulfoxide/acetone

Scheme 24. Mn-catalyzed radical Brook rearrangement of allyl alcohols

Scheme 25. [3＋2] cyclization reaction of allyl alcohols with sec-alcohols

Scheme 26. Three-component [3＋2＋1] annulation of allyl alcohols, ketones and ammonium acetate

Scheme 27. The possible mechanism of phosphonylation of allyl alcohols

Scheme 28. Silver-catalyzed carbonphosphinylation of allyl alcohols

Scheme 29. Visible-light-promoted carbophosphinylation of allyl alcohols

Scheme 30. Visible-light-induced phosphorus radical involved semipinacol rearrangement reaction

Scheme 31. Possible mechanism of alkyl esterification of allyl alcohols

Scheme 32. Cross-coupling of allyl alcohols with α-bromo- carbonyls

Scheme 33. Visible light-mediated arylalkylation of allyl alcohols with α-bromo diethyl malonate

Scheme 34. Visible light-promoted carbodifluoroalkylation of allyl alcohols

Scheme 35. Carbodifluoroalkylation of allyl alcohols with bromodifluoroacetate

Scheme 36. Cu2O-catalyzed phosphonyldifluoromethylation of allyl alcohols

Scheme 37. Cu-catalyzed silication of allyl alcohols

Scheme 38. Fe(III)-mediated radical 1,2-aryl migration of allyl alcohols

Scheme 39. Cu-catalyzed amination-induced 1,2-migration of allyl alcohols

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