Visible-Light-Induced Intramolecular C(sp2)-H Amination and Aziridination of Azidoformates via a Triplet Nitrene Pathway

被引：42

作者：

Zhang, Yipin ^{[1
]}

Dong, Xunqing ^{[1
]}

Wu, Yanan ^{[1
]}

Li, Guigen ^{[2
]}

Lu, Hongjian ^{[1
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, Jiangsu Key Lab Adv Organ Mat, Inst Chem & BioMed Sci, Nanjing 210023, Jiangsu, Peoples R China

[2] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 16期

基金：

中国国家自然科学基金;

关键词：

C-H AMINATION; ALKENE AZIRIDINATION; HIGHLY EFFICIENT; ORGANIC AZIDES; CATALYST; AMIDATION; SULFONAMIDES; OXIDATION; ARENES; FUNCTIONALIZATION;

D O I：

10.1021/acs.orglett.8b01980

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic intramolecular C-H amination and aziridination reactions of o-allylphenyl azidoformates have been achieved under visible-light irradiation, providing a mild, clean, and efficient method for the synthesis of useful benzoxazolones and [5.1.0] bicyclic aziridines. Mechanistic studies suggest that a triplet nitrene acts as the reactive intermediate. The chemoselectivity of the reaction, with alkyl olefin aziridination >> electron deficient olefin aziridination approximate to C(sp(2))-H arnination >> C(sp(3))-H amination was observed, which may be instructive in the development of an understanding of visible-light-induced triplet nitrene transformation reactions.

引用

页码：4838 / 4842

页数：5

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