基于α-羰基重氮化合物参与的N-H插入反应的研究进展

doi:10.6023/cjoc201904044

摘要/Abstract

α-羰基重氮化合物易于制备，在光照和加热等条件下脱去氮气形成高反应活性的卡宾中间体，通过卡宾介导的各类反应可以高效构筑多种化学键，其中N-H插入反应可以实现高效构筑C-N键，在有机合成和药物合成领域得到广泛应用.总结了在过渡金属、有机小分子、生物大分子催化及光和热条件下实现α-羰基重氮化合物对N-H键的插入反应的研究进展，主要介绍了反应机理和合成应用，并对发展前景进行展望.

关键词: α-羰基重氮化合物, 卡宾, N-H插入反应, C-N键

The α-diazocarbonyl compounds are easy to prepare and can be dediazonized to highly reactive carbene intermediates under thermolytic or photolytic conditions. Chemical bonds can be efficiently constructed by carbene mediated reactions, including the insertion reaction of carbene into N-H bonds which is an effective method for constructing C-N bonds. The α-diazocarbonyl compounds have received extensive application in organic synthesis and pharmaceutical synthesis. The research progress in the insertion reaction of α-diazocarbonyl compounds into N-H bonds under transition metal, organic small molecules, biomacromolecule or photolytic and thermolytic conditions is summarized, including the reaction mechanism and synthesis applications. Finally, the prospects of this reaction are also discussed.

Key words: α-diazocarbonyl compound, carbene, N-H insertion reaction, C-N bond

引用此文

封佳俊, 易享炎, 傅耀锋, 于杨, 黄菲. 基于α-羰基重氮化合物参与的N-H插入反应的研究进展[J]. 有机化学, 2019, 39(11): 3013-3025.

Feng Jiajun, Yi Xiangyan, Fu Yaofeng, Yu Yang, Huang Fei. Progress in N-H Insertion Reaction of α-Diazocarbonyl Compounds[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3013-3025.

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图/表 28

图式 1. α-羰基重氮化合物的反应活性

Schema 1. Reactivity of α-diazocarbonyl compounds

图式 2. N—H插入反应构筑C—N键化合物

Schema 2. N—H insertion to construct C—N bond compounds

图式 3. Cu(Ⅰ)-磷配体催化N—H插入反应

Schema 3. Cu(Ⅰ)-phosphine complexes catalyzed N—H insertion reaction

图式 4. 吲哚酮和2-喹啉酮类化合物的合成

Schema 4. Synthesis of indolones and 2-quinolinones

图式 5. 5步反应不对称全合成(－)-goniomitine

Schema 5. Five-step asymmetric total synthesis of (－)-goniomitine

图式 6. Rh2(OAc)4催化四种脱氧核苷酸的N—H插入反应

Schema 6. Rh2(OAc)4-catalyzed N—H insertion reaction of a tetradeoxynucleotide

图式 7. [Ru(Por)(NHC)2)]配合物催化N—H插入反应

Schema 7. [Ru(Por)(NHC)2)] complexes catalyzed N—H insertion reaction

图式 8. 铁卟啉催化氨气和醋酸铵N—H键的插入反应

Schema 8. Iron porphyrin catalyzed N—H insertion of ammonia and ammonium acetate

图式 9. 铱催化N—H插入反应

Schema 9. Iridium-catalyzed N—H insertion reaction

图式 10. 铜配合物催化不对称N—H插入反应

Schema 10. Copper complexes catalyzed asymmetric N—H insertion reaction

图式 11. CuCl和手性螺环双噁唑啉催化不对称N—H插入反应

Schema 11. Asymmetric N—H insertion reaction catalyzed by CuCl and chiral spiro bisoxazolines

图式 12. 铜催化不对称N—H插入反应可能的机理

Schema 12. Proposed mechanism for copper-catalyzed asymmetric N—H insertion reaction

图式 13. CuBr和双联吡啶催化不对称N—H插入反应

Schema 13. Asymmetric N—H insertion reaction catalyzed by CuCl and bipyridine

图式 14. CuCl和联萘酚衍生物催化不对称N—H插入反应

Schema 14. Asymmetric N—H insertion reaction catalyzed by CuCl and binol derivative

图式 15. Pd催化不对称N—H插入反应

Schema 15. Palldium-catalyzed asymmetric N—H insertion reaction

图式 16. Rh2(TPA)4和手性螺环磷酸催化不对称N—H插入反应

Schema 16. Asymmetric N—H insertion reaction catalyzed by Rh2(TPA)4 and chiral spiro phosphoric acid

图式 17. Rh2(TPA)4和手性螺环磷酸协同催化N—H插入反应的可能机理

Schema 17. Proposed mechanism for Rh2(TPA)4 and chiral spiro phosphoric acid co-catalyzed N—H insertion reaction

图式 18. N—H插入反应合成高对映选择性的α-烯基-α-氨基酸

Schema 18. Enantioselective synthesis of α-alkenyl α-amino acids via N—H insertion reaction

图式 19. 合成γ-硝基-α-氨基琥珀酸酯类化合物和3-氨基吡咯烷酮类衍生物

Schema 19. Synthesis of γ-nitro-α-amino-succinates and 3-aminopyrrolidinone derivatives

图式 20. 合成多取代的吡咯烷

Schema 20. Synthesis of highly substituted pyrrolidines

图式 21. 有机小分子催化N—H插入反应

Schema 21. N—H insertion reaction catalyzed by organic small molecules

图式 22. 脲类化合物催化N—H插入反应可能的机理

Schema 21. Proposed mechanism for Urea-catalyzed N—H insertion reaction

图式 23. P450-BM3催化N—H插入反应

Schema 23. N—H insertion reaction catalyzed by P450-BM3

图式 24. 肌红蛋白催化N—H插入反应

Schema 24. Myoglobin-catalyzed N—H insertion reaction

图式 25. 血红素催化N—H插入反应可能的机理

Schema 25. Proposed mechanism for Hemin-catalyzed N—H insertion reaction

图式 26. 加热条件下实现N—H插入反应

Schema 26. N—H insertion reaction under thermal condition

图式 27. 蓝光促进芳基重氮酯光解实现N—H插入反应

Schema 27. Blue light-promoted photolysis of aryldiazoacetates to achieve N—H insertion reaction

图式 28. 蓝光条件下实现N—H插入反应可能的机理

Schema 28. Proposed mechanism for N—H insertion reaction under blue light condition

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