自由基介导的α,α-二芳基烯丙醇1,2-芳基迁移反应研究进展

doi:10.6023/cjoc202208028

摘要/Abstract

作为一种广泛使用的结构单元, 烯丙醇无需预官能化即可直接参与合成反应. 近年来, 烯丙醇的迁移反应得到了极大的关注, 这类反应往往通过半频哪醇或neophyl重排等方式实现, 为各种重要羰基化合物的合成提供了一种强有力的策略. 系统综述了二芳基烯丙醇作为合成子时, 涉及自由基引发基团迁移反应的最新进展, 讨论了反应范围、局限性以及部分机理, 并对该领域存在的挑战以及未来发展趋势进行展望.

关键词: 烯丙醇, 迁移反应, 半频哪醇, neophyl重排, 羰基化合物

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

引用此文

张建涛, 邓雅文, 莫诺琳, 陈莲芬. 自由基介导的α,α-二芳基烯丙醇1,2-芳基迁移反应研究进展[J]. 有机化学, 2023, 43(2): 426-435.

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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图/表 39

图式1. 自由基介导的烯丙醇1,2-迁移反应

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

图式2. 烯丙醇的三氟甲基化反应机理

Scheme 2. Possible mechanism of trifluoromethylation of allyl alcohols

图式3. 金属催化烯丙醇的三氟甲基化反应

Scheme 3. Metal-catalyzed trifluoromethylation of allyl alcohols

图式4. 无金属催化的烯丙醇三氟甲基化反应

Scheme 4. Metal-free trifluoromethylation of allyl alcohols

图式5. 可见光启动烯丙醇三氟甲基化反应

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

图式6. 可见光诱导烯丙醇三氟甲基化反应

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

图式7. 电化学氧化烯丙醇的三氟甲基化反应

Scheme 7. Electrochemical oxidative trifluoromethylation of allyl alcohols

图式8. 铜催化烯丙醇的全氟烷基化反应

Scheme 8. Cu-catalyzed perfluoroalkylation of allyl alcohols

图式9. 三氟甲烷硫醇银介导烯丙醇的三氟甲基硫醇化反应

Scheme 9. AgSCF3-mediated trifluoromethylthiolation of allyl alcohol

图式10. 烯丙醇氰烷基化反应机理

Scheme 10. Possible mechanism of cyanoalkylation of allyl alcohols

图式11. 铜催化烯丙醇与烷基腈的氰烷基化反应

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

图式12. TBPB介导烯丙醇与乙腈的氰烷基化反应

Scheme 12. TBPB-mediated of allyl alcohols with acetonitrile

图式13. 可见光诱导烯丙醇与烷基腈的氰烷基化反应

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

图式14. 烯丙醇酰基化化反应机理

Scheme 14. Possible mechanism of acylation of allyl alcohols

图式15. 紫外光促进烯丙醇与α-酮醇的芳酰基化反应

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

图式16. 烯丙醇与芳基醛的氧化酰化反应

Scheme 16. Oxidative acylation of allyl alcohols with aryl aldehydes

图式17. 未活化烯烃的光催化自由基芳酰化反应

Scheme 17. Photocatalytic radical aroylation of unactivated alkenes

图式18. 烯丙醇与醛的自由基1,2-烷基芳基化/酰芳基化

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

图式19. TBPB促进烯丙醇与醚的自由基烷基化反应

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

图式20. DTBP促进烯丙醇与烷烃的烷基化反应

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

图式21. 烯丙醇的烷基化反应

Scheme 21. Possible mechanism of alkylation of allyl alcohols

图式22. 镍催化烯丙醇与酰胺的烷酰胺化反应

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

图式23. 可见光促进烯丙醇与二甲亚砜/丙酮的烷基化反应

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

图式24. 锰催化烯丙醇自由基布鲁克重排反应

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

图式25. 烯丙醇与仲醇[3＋2]环化反应

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

图式26. 烯丙醇、酮和乙酸铵的三组分[3＋2＋1]环化反应

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

图式27. 烯丙醇膦酰基化化反应机理

Scheme 27. The possible mechanism of phosphonylation of allyl alcohols

图式28. 银催化烯丙醇的碳磷酰化反应

Scheme 28. Silver-catalyzed carbonphosphinylation of allyl alcohols

图式29. 可见光促进烯丙醇的碳膦酰化反应

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

图式30. 可见光诱导磷自由基参与半频哪醇重排反应

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

图式31. 烯丙醇的烷基酯化反应机理

Scheme 31. Possible mechanism of alkyl esterification of allyl alcohols

图式32. 烯丙醇与α-溴代羰基物的交叉偶联反应

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

图式33. 可见光介导的烯丙醇与α-溴代丙二酸二乙酯的芳基烷基化反应

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

图式34. 可见光促进烯丙醇的碳二氟烷基化反应

Scheme 34. Visible light-promoted carbodifluoroalkylation of allyl alcohols

图式35. 烯丙醇与溴二氟乙酸酯的碳二氟烷基化反应

Scheme 35. Carbodifluoroalkylation of allyl alcohols with bromodifluoroacetate

图式36. 氧化亚铜催化烯丙醇的膦酰基二氟甲基化反应

Scheme 36. Cu2O-catalyzed phosphonyldifluoromethylation of allyl alcohols

图式37. 铜催化烯丙醇的硅基化反应

Scheme 37. Cu-catalyzed silication of allyl alcohols

图式38. 三价铁介导的烯丙醇自由基1,2-芳基迁移反应

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

图式39. 铜催化胺化诱导的烯丙醇1,2-迁移反应

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

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