Lewis Base-Boryl Radicals Enabled the Desulfurizative Reduction and Annulation of Thioamides

被引：36

作者：

Yu, You-Jie

Zhang, Feng-Lian

Cheng, Jie

Hei, Jing-Hao

Deng, Wei-Ting

Wang, Yi-Feng ^{[1
]}

机构：

[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, 96 Jinzhai Rd, Hefei 230026, Anhui, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 01期

基金：

中国博士后科学基金;

关键词：

HETEROCYCLIC CARBENE BORANES; STEREOCONTROLLED TOTAL-SYNTHESIS; POLARITY-REVERSAL CATALYSIS; HYDROGEN; PHOTOPOLYMERIZATIONS; COMPLEXES; N; N-DIMETHYLTHIOFORMAMIDE; COORDINATION; ABSTRACTION; CYCLIZATION;

D O I：

10.1021/acs.orglett.7b03201

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new protocol for radical transformations of thioamides promoted by Lewis base-boryl radicals is reported. The desulfurizative reduction to access organic amines was enabled utilizing 4-dimethylaminopyridine-BH3 as the boryl radical precursor and PhSH as the polarity reversal catalyst. Alternatively, the chain process for unsaturated thioamides was switched to an annulation reaction using N-heterocyclic carbene BH3 as the boryl radical precursor and sterically bulky Ph3CSH as the catalyst, allowing for the construction of N-heterocyclic and carbocyclic skeletons.

引用

页码：24 / 27

页数：4

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