Synlett 2013; 24(11): 1443-1447
DOI: 10.1055/s-0033-1338939
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Aryl Thiocyanates via Copper-Catalyzed Aerobic Oxidative Cross-Coupling between Arylboronic Acids and KSCN

Nan Sun
a   College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Fax: +86(571)88320103   Email: xinquan@zjut.edu.cn
,
Han Zhang
a   College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Fax: +86(571)88320103   Email: xinquan@zjut.edu.cn
,
Weimin Mo
a   College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Fax: +86(571)88320103   Email: xinquan@zjut.edu.cn
,
Baoxiang Hu
a   College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Fax: +86(571)88320103   Email: xinquan@zjut.edu.cn
,
Zhenlu Shen
a   College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Fax: +86(571)88320103   Email: xinquan@zjut.edu.cn
,
Xinquan Hu*
a   College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Fax: +86(571)88320103   Email: xinquan@zjut.edu.cn
b   State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 16 March 2013

Accepted after revision: 17 April 2013

Publication Date:
15 May 2013 (online)


Preview

Abstract

A new protocol for the preparation of aryl thiocyanates by the cross-coupling reaction of arylboronic acids with KSCN salt is described. The coupling reaction was catalyzed by 20 mol% of copper acetate in the presence of 2.0 equivalents 4-methylpyridine serving both as ligand and base under 0.2 MPa of molecular oxygen. A variety of arylboronic acids, including those with substituents at ortho position, were suitable under the reaction conditions.

Supporting Information