Transition-Metal-Free Thioamination of Arynes Using Sulfenamides

被引：43

作者：

Gaykar, Rahul N. ^{[1
]}

Bhattacharjee, Subrata ^{[1
]}

Biju, Akkattu T. ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 03期

关键词：

STEVENS REARRANGEMENT; AROMATIC-COMPOUNDS; ACCESS; INSERTION; SULFIDES; BENZYNE; ACTIVATION; CHEMISTRY; MECHANISM; CARBON;

D O I：

10.1021/acs.orglett.8b03966

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The insertion of arynes into the S-N sigma-bond of sulfenamides allowing the synthesis of o-sulfanylaniline derivatives with reasonable functional group compatibility is presented. The aryne generated from 2-(trimethylsilyl)aryl triflates using CsF in DME was the key for the success of this transition-metal-free thioamination reaction, which involves new C-N and C-S bond formations in a single step under mild conditions. Moreover, the synthetic potential of this method was demonstrated by the synthesis of the antidepressant drug vortioxetine.

引用

页码：737 / 740

页数：4

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