General and Practical Formation of Thiocyanates from Thiols

被引：91

作者：

Frei, Reto

Courant, Thibaut ^{[1
]}

Wodrich, Matthew D. ^{[1
]}

Waser, Jerome ^{[1
]}

机构：

[1] EPFL SB ISIC LCSO, Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, CH-1015 Lausanne, Switzerland

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 06期

基金：

欧洲研究理事会;

关键词：

chemoselectivity; cyanation; hypervalent iodine; thiocyanates; synthetic methods; HIGHLY STEREOSPECIFIC METHOD; HYPERVALENT IODINE REAGENTS; DIRECT CYANATION; ORGANIC THIOCYANATES; DENSITY FUNCTIONALS; ARYL THIOCYANATES; M06; SUITE; CHEMISTRY; CYANO; ALKYNYLATION;

D O I：

10.1002/chem.201406171

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new method for the cyanation of thiols and disulfides using cyanobenziodoxol(on)e hypervalent iodine reagents is described. Both aliphatic and aromatic thiocyanates can be accessed in good yields in a few minutes at room temperature starting from a broad range of thiols with high chemioselectivity. The complete conversion of disulfides to thiocyanates was also possible. Preliminary computational studies indicated a low energy concerted transition state for the cyanation of the thiolate anion or radical. The developed thiocyanate synthesis has broad potential for various applications in synthetic chemistry, chemical biology and materials science.

引用

页码：2662 / 2668

页数：7

共 76 条

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