Silver-Catalyzed Stereoselective Aminosulfonylation of Alkynes

被引：134
|
作者：
Ning, Yongquan [1 ]
Ji, Qinghe [1 ]
Liao, Peiqiu [1 ]
Anderson, Edward A. [3 ]
Bi, Xihe [1 ,2 ]
机构：
[1] Northeast Normal Univ, Jilin Prov Key Lab Organ Funct Mol Design & Synth, Dept Chem, Changchun 130024, Jilin, Peoples R China
[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
[3] Univ Oxford, Chem Res Lab, 12 Mansfield Rd, Oxford OX1 3TA, England
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 44期
基金：
英国工程与自然科学研究理事会;
关键词：
alkynes; aminosulfonylation; radical reactions; silver catalysis; stereoselectivity; BETA-KETO SULFONES; C BOND-CLEAVAGE; TERMINAL ALKYNES; PROPARGYLIC ALCOHOLS; RADICAL-ADDITION; VINYL AZIDES; EFFICIENT; TRIFLUOROMETHYLATION; DIFUNCTIONALIZATION; NITROGENATION;
D O I：
10.1002/anie.201705122
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A silver-catalyzed intermolecular aminosulfonylation of terminal alkynes with sodium sulfinates and TMSN3 is reported. This three-component reaction proceeds through sequential hydroazidation of the terminal alkyne and addition of a sulfonyl radical to the resultant vinyl azide. The method enables the stereoselective synthesis of a wide range of beta-sulfonyl enamines without electron-withdrawing groups on the nitrogen atom. These enamines are found to be suitable for a variety of further transformations.
引用
收藏
页码：13805 / 13808
页数：4
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