A mild copper-catalyzed aerobic oxidative thiocyanation of arylboronic acids with TMSNCS. Issue 3 (27th November 2014)

• Record Type: Journal Article
• Authors: Sun, Nan; Che, Liusheng; Mo, Weimin; Hu, Baoxiang; Shen, Zhenlu; Hu, Xinquan
• Is Part Of: Organic & biomolecular chemistry. Volume 13:Issue 3(2015)
• Page Start: 691
• Page End: 696
• Publication Date: 2014-11-27
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c4ob02208d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A facile and generalized synthesis of aryl thiocyanates has been established via the CuCl-catalyzed oxidative coupling of arylboronic acids with TMSNCS. The reaction could be conducted at RT and under an O2 atmosphere. Abstract : A facile and efficient transformation of arylboronic acids to their corresponding aryl thiocyanates has been successfully developed. Based on the CuCl-catalyzed oxidative cross-coupling reaction between arylboronic acids and trimethylsilylisothiocyanate (TMSNCS) under oxygen atmosphere, the transformation can be readily conducted at ambient temperature. The newly-developed protocol provided a competitive synthetic approach to aryl thiocyanates that can tolerate a broad range of reactive functional groups and/or strong electron-withdrawing groups.