Synthesis 2015; 47(23): 3741-3745
DOI: 10.1055/s-0035-1560458
paper
© Georg Thieme Verlag Stuttgart · New York

Copper Nanoparticle Catalyzed Formation of C–S Bonds through Activation of S–S and C–H Bonds: An Easy Route to Alkynyl Sulfides­

Balaji Mohan
Department of Chemistry, Pusan National University, Busan, 609735, South Korea   Email: chemistry@pusan.ac.kr
,
Sori Hwang
Department of Chemistry, Pusan National University, Busan, 609735, South Korea   Email: chemistry@pusan.ac.kr
,
Hyunje Woo
Department of Chemistry, Pusan National University, Busan, 609735, South Korea   Email: chemistry@pusan.ac.kr
,
Kang Hyun Park*
Department of Chemistry, Pusan National University, Busan, 609735, South Korea   Email: chemistry@pusan.ac.kr
› Author Affiliations
Further Information

Publication History

Received: 10 May 2015

Accepted after revision: 16 July 2015

Publication Date:
21 August 2015 (online)


Abstract

An efficient method for copper nanoparticle catalyzed ligand-free S–Csp bond formation was developed by using dimethyl sulfoxide as the solvent, a base, and molecular oxygen as a green oxidant. This study provides a new catalytic route for the production of alkynyl sulfides through dual activation of S–S and C–H bonds. A wide range of alkynyl sulfides were synthesized on a large scale with a low catalyst loading (0.5 mol% Cu). This synthetic methodology could also be extended to selenides, whereas tellurides underwent analogous reactions in the absence of a catalyst.

Supporting Information