Palladium and copper co-catalyzed Markovnikov hydrothiolation of terminal olefins and alkynes》.pdfVIP

Tetrahedron Letters 56 (2015) 6022–6029 Contents lists available at ScienceDirect Tetrahedron Letters journal homepage: /locate/tetlet Palladium and copper co-catalyzed Markovnikov hydrothiolation of terminal olefins and alkynes Haojie Ma, Xiaoyu Ren, Xiaoqiang Zhou, Chaowei Ma, Yongqin He, GuoSheng Huang ⇑ State Key Laboratory of Applied Organic Chemistry, Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province, Department of Chemistry, Lanzhou University, Lanzhou 730000, China a r t i c l e i n f o a b s t r a c t Article history: A simple and efficient method for palladium and copper co-catalyzed Markovnikov hydrothiolation of Received 7 August 2015 thiols to olefins or alkynes has been developed. The reaction allows olefins or alkynes bearing various Revised 11 September 2015 functional groups to react with different thiols, providing good to excellent yields of alkyl sulfides or vinyl Accepted 15 September 2015 sulfides. A proposed mechanistic study indicated that Cu(II) plays a key role in obtaining Markovnikov Available online 15 September 2015 products. 2015 Elsevier Ltd. All rights reserved. Keywords: Markovnikov hydrothiolation Thiols Olefins or alkynes Alkyl sulfides or vinyl sulfides Introduction (1-bromoethyl)benzene