Progress in N-H Insertion Reaction of α-Diazocarbonyl Compounds

doi:10.6023/cjoc201904044

Abstract

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

Cite this article

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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Fig. & Tab. 28

Schema 1. Reactivity of α-diazocarbonyl compounds

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

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

Schema 4. Synthesis of indolones and 2-quinolinones

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

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

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

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

Schema 9. Iridium-catalyzed N—H insertion reaction

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

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

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

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

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

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

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

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

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

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

Schema 20. Synthesis of highly substituted pyrrolidines

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

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

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

Schema 24. Myoglobin-catalyzed N—H insertion reaction

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

Schema 26. N—H insertion reaction under thermal condition

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

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

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