可见光催化偕二氟烯烃碳-氟键官能化反应的研究进展

doi:10.6023/cjoc202106013

摘要/Abstract

单氟烯烃结构单元广泛存在于药物及天然产物等复杂功能分子中, 同时也是重要的有机合成子, 在医药、生物和材料等领域具有广泛的应用. 因此, 开发绿色、经济且高效的合成单氟烯烃化合物的方法具有重要的科学意义和现实价值. 偕二氟烯烃C—F键官能化是制备单氟烯烃化合物的有效手段, 总结了在可见光氧化还原催化、可见光氧化还原/过渡金属协同催化条件下实现偕二氟烯烃C—F键官能化反应的研究进展, 主要介绍了底物适用范围、反应机理和合成应用, 并对它的发展前景进行了展望.

关键词: 可见光, 单氟烯烃, 偕二氟烯烃, C—F键官能化

Monofluoroalkene structural units widely exist in complex functional molecules such as drugs and natural products. They are also critical organic synthons with broad applications in medicine, biology, materials and other fields. Therefore, it is of great scientific significance and practical value to develop green, economical and efficient methods for synthesizing monofluoroalkenes. Functionalization of the C—F bond of gem-difluoroalkenes is an effective method to prepare monofluoroalkenes. The research progress in C—F bond functionalization of gem-difluoroalkenes under visible-light redox catalysis and visible-light redox/transition-metal synergistic catalysis, including the substrate scope, reaction mechanism, and synthesis applications, is summarized. Finally, the prospects of this reaction are also discussed.

Key words: visible-light, monofluoroalkene, gem-difluoroalkene, C—F bond functionalization

引用此文

李志清, 邱潇杨, 娄江, 王强. 可见光催化偕二氟烯烃碳-氟键官能化反应的研究进展[J]. 有机化学, 2021, 41(11): 4192-4207.

Zhiqing Li, Xiaoyang Qiu, Jiang Lou, Qiang Wang. Progress in Visible-Light Catalyzed C—F Bond Functionalization of gem-Difluoroalkenes[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4192-4207.

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图/表 29

图1. 含单氟烯烃结构单元的代表性生物活性分子

Figure 1. Representative bioactive molecules containing monofluoroalkene structural units

图式1. 可见光催化偕二氟烯烃C—F键官能化

Scheme 1. Visible-light catalyzed C—F bond functionalization of gem-difluoroalkenes

图式2. 可见光氧化还原催化C(sp2)—F键α-胺甲基化

Scheme 2. Visible-light photoredox catalyzed α-aminomethyl- ation of C(sp2)—F bond

图式3. 光氧化还原催化偕二氟烯烃α-胺甲基化机理研究

Scheme 3. Mechanistic studies of photoredox catalyzed α- aminomethylation of gem-difluoroalkenes

图式4. 偕二氟烯烃α-胺甲基化的反应机理

Scheme 4. Reaction mechanism of α-aminomethylation of gem- difluoroalkenes

图式5. 可见光催化杂原子烷烃α位C—H键的单氟烯基化

Scheme 5. Photoredox-catalyzed α-monofluoroalkenylation of heteroatomic alkanes

图式6. 杂原子烷烃α-单氟烯基化的反应机理

Scheme 6. Reaction mechanism of α?monofluoroalkenylation of heteroatomic alkanes

图式7. 可见光催化α-氨基酸脱羧单氟烯基化

Scheme 7. Visible-light catalyzed decarboxylative monofluoroalkenylation of α-amino acids

图式8. α-氨基酸脱羧单氟烯基化反应机理

Scheme 8. Reaction mechanism of decarboxylative monofluoroalkenylation of α-amino acids

图式9. 可见光催化偕二氟烯烃和烷基羧酸的脱羧偶联反应

Scheme 9. Visible-light catalyzed decarboxylative cross-coupling of gem-difluoroalkenes with aliphatic carboxylic acids

图式10. 环丙基乙酸参与的自由基钟反应

Scheme 10. Radical clock reaction involving cyclopropylacetic acid

图式11. 自由基脱羧交叉偶联反应机理

Scheme 11. Reaction mechanism of decarboxylative radical cross-coupling

图式12. 可见光催化偕二氟烯烃的脱氟烷基化

Scheme 12. Visible-light catalyzed defluorinative alkylation of gem-difluoroalkenes

图式13. 可见光促进偕二氟烯烃的脱氟烷基化机理研究

Scheme 13. Mechanism studies for visible-light promoted defluorinative alkylation of gem-difluoroalkenes

图式14. 可见光促进偕二氟烯烃脱氟烷基化的反应机理

Scheme 14. Possible mechanism for visible-light promoted defluorinative alkylation of gem-difluoroalkenes

图式15. 可见光催化三组分串联反应

Scheme 15. Three-component tandem reactions catalyzed by visible-light

图式16. 可见光催化三组分串联反应机理

Scheme 16. Reaction mechanism of three-component tandem reactions catalyzed by visible-light

图式17. 可见光诱导偕二氟烯烃选择性脱氟硼化反应

Scheme 17. Visible-light-induced selective defluoroborylation of gem-difluoroalkenes

图式18. 选择性脱氟硼化反应机理

Scheme 18. Reaction mechanism of selective defluoroborylation

图式19. 可见光/钯协同催化C—F键羧基化

Scheme 19. Visible-light/palladium co-catalyzed C—F bond carboxylation

图式20. 芳基酮参与的脱氟羧基化反应

Scheme 20. Defluorocarboxylation of aryl ketones

图式21. 芳基酮参与的脱氟羧基化反应机理研究

Scheme 21. Mechanistic studies of defluorocarboxylation of aryl ketones

图式22. 芳基酮参与的脱氟羧基化反应机理

Scheme 22. Reaction mechanism of defluorocarboxylation of aryl ketones

图式23. 可见光催化偕二氟烯烃C—F键三氟甲基化

Scheme 23. Visible-light catalyzed trifluoromethylation of C—F bond of gem-difluoroalkenes

图式24. 偕二氟烯烃C—F键三氟甲基化反应机理

Scheme 24. Reaction mechanism for trifluoromethylation of C—F bond of gem-difluoroalkenes

图式25. 可见光催化偕二氟烯烃与硫醇的脱氟交叉偶联反应

Scheme 25. Visible-light catalyzed defluorinative cross-coupling of gem-difluoroalkenes with thiols

图式26. 偕二氟烯烃与硫醇的脱氟交叉偶联反应机理

Scheme 26. Reaction mechanism for the defluorinative cross- coupling of gem-difluoroalkenes with thiols

图式27. 可见光催化α-氟-β-芳基烯基硫醚的合成

Scheme 27. Visible-light catalyzed the synthesis of α-fluoro- β-arylalkenyl sulfides

图式28. α-氟-β-芳基烯基硫醚合成的反应机理

Scheme 28. Reaction mechanism for the synthesis of α-fluoro- β-arylalkenyl sulfides

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