Metal-catalyzed electrochemical diazidation of alkenes

被引：573

作者：

Fu, Niankai ^{[1
]}

Sauer, Gregory S. ^{[1
]}

Saha, Ambarneil ^{[1
]}

Loo, Aaron ^{[1
]}

Lin, Song ^{[1
]}

机构：

[1] Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA

来源：

SCIENCE | 2017年 / 357卷 / 6351期

关键词：

ORGANIC ELECTROCHEMISTRY; VICINAL DIAMINATION; CONVENIENT ACCESS; OXIDATION; OLEFINS; 1,2-DIAMINATION; COMPLEXES; AMINATION; ADDITIONS;

D O I：

10.1126/science.aan6206

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Vicinal diamines are a common structural motif in bioactive natural products, therapeutic agents, and molecular catalysts, motivating the continuing development of efficient, selective, and sustainable technologies for their preparation. We report an operationally simple and environmentally friendly protocol that converts alkenes and sodium azide-both readily available feedstocks-to 1,2-diazides. Powered by electricity and catalyzed by Earth-abundant manganese, this transformation proceeds under mild conditions and exhibits exceptional substrate generality and functional group compatibility. Using standard protocols, the resultant 1,2-diazides can be smoothly reduced to vicinal diamines in a single step, with high chemoselectivity. Mechanistic studies are consistent with metal-mediated azidyl radical transfer as the predominant pathway, enabling dual carbon-nitrogen bond formation.

引用

页码：575 / 579

页数：5

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