Trifluoromethylthiolation of Diazo Compounds through Copper Carbene Migratory Insertion. Issue 15 (18th March 2014)

• Record Type: Journal Article
• Authors: Wang, Xi; Zhou, Yujing; Ji, Guojing; Wu, Guojiao; Li, Ming; Zhang, Yan; Wang, Jianbo
• Is Part Of: European journal of organic chemistry. Issue 15(2014)
• Page Start: 3093
• Page End: 3096
• Publication Date: 2014-03-18
• Subjects: Diazo compounds -- Carbenes -- Fluorine -- Migratory insertion; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402105
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A strategy to introduce the SCF3 group through the Cu I ‐promoted reaction of diazo compounds with the nucleophilic AgSCF3 trifluoromethylthiolation reagent was developed. Various diazo compounds were smoothly converted under mild conditions to form the C(sp 3 )–SCF3 bond. Mechanistically, migratory insertion of SCF3 ‐bearing Cu carbene intermediates is involved in this transformation. Abstract : A strategy to introduce the SCF3 group through the Cu I ‐promoted reaction of diazo compounds with the nucleophilic AgSCF3 trifluoromethylthiolation reagent is developed. Various diazo compounds are smoothly converted under mild conditions to form the C(sp 3 )–SCF3 bond. Migratory insertion of SCF3 ‐bearing Cu I carbene intermediates is proposed as the key step in this transformation.