Access to CyclicN-Trifluoromethyl Ureas through PhotocatalyticActivation of Carbamoyl Azides

被引：44

作者：

Bouayad-Gervais, Samir ^{[1
]}

Nielsen, Christian D-T ^{[1
]}

Turksoy, Abdurrahman ^{[1
]}

Sperger, Theresa ^{[1
]}

Deckers, Kristina ^{[1
]}

Schoenebeck, Franziska ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2022年 / 144卷 / 13期

基金：

欧洲研究理事会;

关键词：

C-H AMINATION; CHEMICAL SPACE; FLUORINE; PHOTOCHEMISTRY; PHOTOCATALYSIS; ISOMERIZATION; EXPLORATION; DERIVATIVES; NITRENES; POTENT;

D O I：

10.1021/jacs.2c02004

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report the mild activation of carbamoyl azidesto the corresponding nitrenes using a blue light/[Ir]-catalyzedstrategy, which enables stereospecific access toN-trifluoromethylimidazolidinones and benzimidazolones. These novel structuralmotifs proved to be highly robust, allowing their downstreamdiversification. On the basis of our combined computational andexperimental studies, we propose that an electron rebound with theexcited metal catalyst is undergone, involving a reduction-triggered nitrogen loss, followed by oxidation to the correspondingcarbamoyl nitrene and subsequent C-H insertion

引用

页码：6100 / 6106

页数：7

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