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炔烃与硫氰酸二苯磺酰亚胺的原子经济性硫氰化-胺化反应

Atom-Economical Thiocyanation-Amination of Alkynes with -Thiocyanato-Dibenzenesulfonimide.

作者信息

Wu Haopeng, Shao Chukai, Wu Di, Jiang Liang, Yin Hongquan, Chen Fu-Xue

机构信息

School of Chemistry & Chemical Engineering, Beijing Institute of Technology (Liangxiang Campus), No. 8 Liangxiang East Road, Fangshan District, Beijing, 102488, China.

State Key Laboratory of Medicinal Chemical Biology, NanKai University, No. 94 Wei Jin Road, Nankai District, Tianjin, 300071, China.

出版信息

J Org Chem. 2021 Apr 2;86(7):5327-5335. doi: 10.1021/acs.joc.0c02780. Epub 2021 Mar 11.

Abstract

A highly regioselective protocol for intermolecular thiocyanation-amination of alkynes by -thiocyano-dibenzenesulfonimide (NTSI) as the SCN and nitrogen sources has been developed. A C-S bond and C-N bond are simultaneously constructed in only one step. The reaction under simple mild conditions features a broad substrate scope, atom economy, high yields (up to 94%), and excellent functional group tolerance.

摘要

已经开发出一种高度区域选择性的方法,用于以β-硫氰基二苯磺酰亚胺(NTSI)作为硫氰根和氮源,对炔烃进行分子间硫氰化-胺化反应。仅一步反应即可同时构建C-S键和C-N键。该反应在简单温和的条件下进行,具有底物范围广、原子经济性高、产率高(高达94%)以及对官能团耐受性优异等特点。

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