可见光诱导重氮化合物产生卡宾及其官能化反应

doi:10.6023/cjoc202109040

摘要/Abstract

卡宾是有机合成中的重要中间体. 在过去的几十年中, 过渡金属催化的卡宾转移反应取得了显著发展. 近年来,可见光促进的重氮化合物通过游离态卡宾的转化也开始兴起. 该类反应仅需要使用可见光作为唯一能源, 符合绿色化学理念. 自2018年Davies课题组和周磊课题组分别独立报道了芳基重氮酯在可见光照射下光解生成游离态卡宾物种以来, 光促重氮化合物的转化反应受到了越来越多科研工作者的关注, 也催生了许多绿色高效的有机合成新反应.在前人工作基础上, 进一步完善了该领域的最新进展, 综述了近期可见光照射下重氮化合物的新转化反应和国内学者的贡献, 展望了该领域的未来发展方向和所面临的挑战.

关键词: 可见光, 重氮化合物, 卡宾, 绿色化学

Carbene is one of the most important synthetic intermediates in organic synthesis. In the past few decades, transition-metal catalyzed carbene transfer reactions have made remarkable development. Recently, visible light-promoted transformation of diazo compounds through the formation of free carbene as key intermediate begun to rise. The reaction only need visible light as the sole energy source which meets the concept of green chemistry. Since the pioneering works developed by the groups of Diaves and Zhou, photo-promoted transformation of diazo compounds has attracted more and more attentions. On the basis of previous work, the latest progress in this field is further improved, which mainly focuses on the recent new transformation reactions of diazo compounds under visible light irradiation and the contributions reported from Chinese research group. The future development direction, as well as challenges in this field is prospected.

Key words: visible light, diazo compound, carbene, green chemistry

引用此文

蔡宝贵, 宣俊. 可见光诱导重氮化合物产生卡宾及其官能化反应[J]. 有机化学, 2021, 41(12): 4565-4574.

Baogui Cai, Jun Xuan. Visible Light-Promoted Transformation of Diazo Compounds via the Formation of Free Carbene as Key Intermediate[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4565-4574.

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图/表 23

图式1. 不同类型重氮化合物的吸收范围

Scheme 1. Absorption range of diverse diazo compounds

图式2. 可见光诱导芳基重氮酯与苯乙烯的环丙烷化反应

Scheme 2. Visible light induced cyclopropanation of aryldiazoacetates with styrene

图式3. 可见光诱导吲哚酮类重氮与芳环的环加成反应

Scheme 3. Visible light induced cyclopropanation of diazooxindoles with arenes

图式4. 连续流动光化学条件下的环丙烷化反应

Scheme 4. Photochemical cyclopropanation under continuous flow conditions

图式5. 可见光促进芳基重氮酯与吲哚衍生物的反应

Scheme 5. Visible light promoted reaction of aryldiazoacetates with indole derivatives

图式6. 可见光促进卡宾对X—H键的插入反应

Scheme 6. Visible light promoted insertion of carbene into X—H bond

图式7. 可见光促进卡宾对肟的插入反应

Scheme 7. Visible light promoted insertion of carbene into oximes

图式8. 可见光促进的芳基重氮酯参与的多组分反应

Scheme 8. Visible light promoted multicomponent reactions involving aryldiazoacetates

图式9. 可见光和碱促进的苯并呋喃衍生物的合成

Scheme 9. Visible light and base promoted synthesis of benzofuran derivatives

图式10. 可见光促进2-吡啶酮的O-烷基化反应

Scheme 10. Visible light promoted O-alkylation 2-pyridinone

图式11. 可见光和碱促进的腙类化合物与芳胺的反应

Scheme 11. Visible light and base promoted reaction of hydrazone compounds with aromatic amines

图式12. 可见光促进芳基重氮酯与苯并三唑的N1-烷基化反应

Scheme 12. Visible light promoted N1-alkylation of aryldiazoacetates with benzotriazoles

图式13. 可见光促进S—H键的插入反应

Scheme 13. Visible light S—H bond insertion reaction

图式14. 可见光促进的Doyle-Kirmse反应

Scheme 14. Visible light promoted Doyle-Kirmse reaction

图式15. 可见光促进芳基重氮酯与二氟烯丙基硫化物的反应

Scheme 15. Visible light promoted reaction of aryldiazoacetates with difluoroallyl sulfides

图式16. 可见光促进亚砜叶立德的合成反应

Scheme 16. Visible light promoted synthesis of sulfoxonium ylides

图式17. 可见光促进4-重氮-1,4-二氢异喹啉-3-酮与烯丙基/炔丙基硫化物的反应

Scheme 17. Visible light promoted reaction of 4-diazo-1,4- dihydroisoquinolin-3-ones with allyl/propargyl sulfide

图式18. 可见光诱导芳基重氮酯、胺、二氧化碳参与的多组分反应

Scheme 18. Visible light induced multicomponent reactions of aryldiazoacetates, amines and carbon dioxide

图式19. 可见光促进芳基重氮酯、肟和四氢呋喃的多组分反应

Scheme 19. Visible light promoted multicomponent reaction of aryldiazoacetates, oximes and tetrahydrofurans

图式20. 可见光促进的硝酮原位产生/重排构建酰胺键

Scheme 20. Visible light promoted in situ generation/ rearrangement of nitrones to construct amide bonds

图式21. 可见光促进氮杂环丙烷和咪唑啉的选择性合成

Scheme 21. Selective synthesis of aziridine and imidazolidine promoted by visible light

图式22. 可见光促进的芳基重氮酯与邻胺基苯乙酮的反应

Scheme 22. Visible light promoted reaction of aryldiazoacetates with o-aminoacetophenones

图式23. 可见光促进重氮化合物的交叉偶联反应

Scheme 23. Visible light promoted coupling of diazo compounds

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