Catalyst‐Free S–S Bond Insertion Reaction of a Donor/Acceptor‐Free Carbene by a Radical Process: A Combined Experimental and Computational Study. Issue 22 (6th July 2016)

• Record Type: Journal Article
• Authors: Zheng, Yang; Bian, Rongjian; Zhang, Xiaolu; Yao, Ruwei; Qiu, Lihua; Bao, Xiaoguang; Xu, Xinfang
• Is Part Of: European journal of organic chemistry. Issue 22(2016)
• Page Start: 3872
• Page End: 3877
• Publication Date: 2016-07-06
• Subjects: Radical reactions -- Donor/aceptor systems -- Carbenes -- Insertion -- Density functional calculations; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600664
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Herein, a donor/acceptor‐free carbene insertion reaction of an S–S bond through a radical process is presented. This catalyst‐free reaction was thermally induced and provided the dithioketal products in moderate to high yields. A mechanism involving radical intermediates was proposed according to the computational study, and these intermediates were verified experimentally and intercepted for the first time by using a cross‐coupling reaction. Abstract : A donor/acceptor‐free carbene insertion reaction of an S–S bond through a radical process is presented. This catalyst‐free reaction was thermally induced and provided the dithioketal products in moderate to high yields. A mechanism involving radical intermediates was proposed according to the computational study, and these intermediates were identified in a cross‐coupling reaction.