Visible-Light-Mediated Umpolung Reactivity of Imines: Ketimine Reductions with Cy2NMe and Water

被引：65

作者：

Wang, Rui ^{[1
]}

Ma, Mengyue ^{[1
]}

Gong, Xu ^{[1
]}

Panetti, Grace B. ^{[2
]}

Fan, Xinyuan ^{[1
]}

Walsh, Patrick J. ^{[1
,2
]}

机构：

[1] Nanjing Tech Univ, Jiangsu Natl Synerget Innovat Ctr Adv Mat, Sch Chem & Mol Engn, Inst Adv Synth, 30 South Puzhu Rd, Nanjing 211816, Jiangsu, Peoples R China

[2] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, 231 South 34th St, Philadelphia, PA 19104 USA

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 08期

基金：

中国国家自然科学基金;

关键词：

PHOTOREDOX CATALYSIS; ASYMMETRIC UMPOLUNG; KETONES; DERIVATIVES; ARYLATION; ALDEHYDES; ALLYLATION; AMINATION; PERYLENE; RADICALS;

D O I：

10.1021/acs.orglett.8b00778

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel carbanionic reactivity of imines mediated by photoredox catalysis is demonstrated. The umpolung imine reactivity is exemplified by proton abstraction from water as a key step in the reduction of benzophenone ketimines to amines (up to 98% yield). Deuterium is introduced into amines efficiently using D2O as an inexpensive deuterium source (>= 95% D ratio). The mechanism of this unusual transformation is probed.

引用

页码：2433 / 2436

页数：4

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