A heterogeneous copper(I)-catalyzed aerobic oxidative cross-dehydrogenative coupling of terminal alkynes with thiols leading to alkynyl sulfides. Issue 46 (18th November 2015)

• Record Type: Journal Article
• Authors: Fang, Zhiqiang; He, Wen; Cai, Mingzhong; Lin, Yang; Zhao, Hong
• Is Part Of: Tetrahedron letters. Volume 56:Issue 46(2015)
• Page Start: 6463
• Page End: 6467
• Publication Date: 2015-11-18
• Subjects: Copper -- Cross-dehydrogenative coupling -- Alkynyl sulfide -- MCM-41 -- Heterogeneous catalysis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.09.153
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: A simple and practical method for a selective synthesis of alkynyl sulfides has been developed through the direct oxidative cross-dehydrogenative coupling of terminal alkynes with thiols in DMSO using a recyclable MCM-41-supported bidentate nitrogen copper(I) complex [MCM-41-2N-CuCl] as catalyst under an atmosphere of oxygen. Highlights: The MCM-41-2N-CuCl complex can be easily prepared by a simple two-step procedure. Heterogeneous Cu-catalyzed CDC reaction of 1-alkynes with thiols is first reported. The reaction generates selectively a variety of alkynyl sulfides in high yields. The Cu catalyst can be recycled 10 times without any decrease in activity. Our catalytic system provides a new, simple, and practical route to alkynyl sulfides. Abstract: A heterogeneous copper-catalyzed direct oxidative cross-dehydrogenative coupling of terminal alkynes with thiols was achieved in DMSO at 70 °C in the presence of an MCM-41-supported bidentate nitrogen copper(I) complex [MCM-41-2N-CuCl] and K2 CO3 under an atmosphere of O2, yielding selectively a variety of alkynyl sulfides in good to excellent yields. This heterogeneous copper catalyst can be easily recovered by a simple filtration and recycled 10 times without any decreases in activity.