Highly regio- and stereoselective synthesis of bis-sulfanyl substituted conjugated dienes by copper–palladium cooperative catalysis. Issue 3 (16th December 2020)

• Record Type: Journal Article
• Authors: Li, Yuan; Wu, Jin; Li, Hui; Sun, Qian; Xiong, Lixue; Yin, Guodong
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 3(2021)
• Page Start: 628
• Page End: 634
• Publication Date: 2020-12-16
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d0qo01256d
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : An efficient one-pot method for the synthesis of ( Z, Z )-isomers of 1, 4-bis(sulfanyl)-1, 4-diaryl-1, 3-butadienes by the cooperative catalysis of Cu(Xantphos)I/Pd(OAc)2 and a base has been developed. Abstract : An efficient one-pot method for the synthesis of symmetric ( Z, Z )-isomers of 1, 4-bis(sulfanyl)-1, 4-diaryl-1, 3-butadienes from the easily available aryl halides, 1, 4-bis(trimethylsilyl)butadiyne and thiols by the cooperative catalysis of Cu(Xantphos)I and Pd(OAc)2 and a base has been developed. Preliminary mechanistic studies revealed that the reaction probably follows the double-Sonogashira coupling/double hydrothiolation pathway, in which two C–C bonds and two C–S bonds were formed sequentially. This protocol features a good substrate scope with a broad range of functional group tolerances, simplicity of operation, and high regio- and stereoselectivity.