重氮化合物作为自由基前体参与的光催化反应

doi:10.6023/cjoc202207016

摘要/Abstract

重氮化合物作为一种用途广泛的合成子而备受化学家的青睐. 在有机合成中, 重氮化合物可以作为卡宾前体1,3-偶极子、C-亲核试剂、末端N-亲电试剂以及自由基中间体等. 近年来, 可见光催化重氮化合物产生自由基及其后续官能化反应取得了长足的进展. 重点综述了近年来在可见光催化下, 重氮化合物作为不同自由基前体参与的有机合成反应. 主要包括光照产生重氮甲基自由基、碳自由基、卡拜自由基和联烯自由基等. 最后对该领域未来的发展方向和面临的挑战做出了展望.

关键词: 光催化, 重氮化合物, 自由基

Diazo compounds are important synthons which have attracted condirable attentions by synthetic chemists. They can server as carbene precursors, 1,3-dipoles, C-nucleophiles, terminal N-electrophiles and radical intermediates. In recent years, the photocatalytic generation of radicals from diazo compounds has made remarkable development. In this review, the recent developments in this research field are summarized which mainly focus on the generation of diazomethyl radical, carbon radicals, carbyne radicals and allene radicals from diazo compounds. Moreover, the future development direction, as well as challenges in this field is prospected.

Key words: photoredox catalysis, diazo compounds, radical

引用此文

谢阳, 宣俊. 重氮化合物作为自由基前体参与的光催化反应[J]. 有机化学, 2022, 42(12): 4247-4256.

Yang Xie, Jun Xuan. Photocatalytic Reactions Involving Diazo Compounds as Radical Precursors[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4247-4256.

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图/表 18

图式1. 光氧化还原催化产生卡拜等价物

Scheme 1. Photoredox generation of carbyne equivalents

图式2. 光氧化还原催化重氮碘试剂合成噁二唑

Scheme 2. Photoredox catalysis synthesis of oxadiazole with diazos iodine reagent

图式3. 光氧化还原催化含CF3基团的噁二唑的合成

Scheme 3. Photoredox catalysis synthesis of oxadiazoles containing CF3

图式4. 光氧化还原催化α-重氮硫三氟甲磺酸盐合成三唑

Scheme 4. Photoredox catalytic α-diazo sulfonium triflates synthesis of triazoles

图式5. 重氮化合物的光氧化还原不对称催化

Scheme 5. Asymmetric and photoredox catalysis of diazo compounds

图式6. 碘催化重氮化合物和烯烃的环丙烷化

Scheme 6. Iodine-catalyzed cyclopropanation of diazo compounds and alkenes

图式7. 碘催化DNA-标记烯烃的环丙烷化

Scheme 7. Iodine-catalyzed cyclopropanation of diazo compounds and alkenes

图式8. 可见光促进重氮酮自由基苯环化

Scheme 8. Visible light-promoted radical benzannulation of diazoketones

图式9. 在无金属和可见光介导条件下合成功能化1-萘酚

Scheme 9. Synthesis of functionalized naphthalene-1-ols under metal-free and visible light-mediated conditions

图式10. 光催化重氮乙酸乙酯对吲哚的C2位烷基化

Scheme 10. Photocatalytic C2 alkylation of indole with ethyl diazoacetate

图式11. 重氮化合物对烯烃官能化经自由基介导的策略

Scheme 11. Radical-mediated strategies for the functionalization of alkenes with diazo compounds

图式12. 重氮化合物的多组分自由基串联Minisci反应

Scheme 12. Radical cascade multicomponent Minisci reactions with diazo compounds

图式13. 重氮化合物的可见光诱导多组分合成γ-氨基酯

Scheme 13. Visible-light-induced multicomponent synthesis of γ?amino esters with diazo compounds

图式14. NHC催化和光催化结合实现烯烃双官能团化

Scheme 14. Combination of NHC catalysis and photocatalysis for bifunctionalization of olefins

图式15. 可见光促进α-重氮酯与H-氧化膦的有氧氧化磷酸化

Scheme 15. Visible-light-promoted aerobic oxyphosphorylation of α-diazoesters with H?phosphine oxides

图式16. 苯乙烯与重氮乙酸乙酯的光催化1,2-氧代烷基化反应

Scheme 16. Photocatalytic 1,2-oxo-alkylation reaction of styrenes with diazoacetates

图式17. 水、炔烃和α-重氮硫盐的三组分偶联

Scheme 17. Three component coupling of alkynes, α?diazo sulfonium triflate and water

图式18. 炔基重氮化合物的可见光促进自由基1,3-双官能化合成四取代的联烯

Scheme 18. Synthesis of tetrasubstituted allenes via visible- light-promoted radical 1,3-difunctionalization of alkynyl diazo compounds

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