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
收藏
页码：737 / 740
页数：4
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