Metal-Free Aziridination of Unactivated Olefins via Transient N-Pyridinium Iminoiodinanes

被引：1

作者：

Tan, Hao ^{[1
]}

Thai, Phong ^{[1
]}

Sengupta, Uddalak ^{[1
]}

Deavenport, Isaac R. ^{[1
]}

Kucifer, Cali M. ^{[1
]}

Powers, David C. ^{[1
]}

机构：

[1] Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA

来源：

JACS AU | 2024年 / 4卷 / 11期

基金：

美国国家卫生研究院;

关键词：

olefin aziridination; iminoiodinane; nitrogen-grouptransfer; C-N coupling; N-aminopyridinium; ELECTROCHEMICAL AZIRIDINATION; CATALYZED AZIRIDINATION; IODINE; MECHANISM; ALCOHOLS; ALKENES; ELUCIDATION; ACTIVATION; CHEMISTRY; EFFICIENT;

D O I：

10.1021/jacsau.4c00556

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We describe a metal-free aziridination of unactivated olefins to generate N-pyridinium aziridines. Subsequent cross-coupling affords N-aryl aziridines, and reductive depyridylation affords N-H aziridines. Kinetics experiments, based on a variable time normalization analysis (VTNA), indicate that aziridination proceeds via a highly electrophilic N-pyridinium iminoiodinane intermediate. These studies expand build-and-couple aziridine synthesis to unactivated olefins and introduce charge-enhanced electrophilicity into the chemistry of iminoiodinanes.

引用

页码：4187 / 4193

页数：7

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