Cs<sub>2</sub>CO<sub>3</sub>-Promoted Hydrothiolation of Alkynes with Aryl Thioureas: Stereoselective Synthesis of (<i>Z</i>)-Vinyl Sulfides
Dan Wang, Han‐Ying Peng, Meng-Meng Yang, Er‐Jun Hao, Yue‐Sheng Li, Zhi‐Bing Dong
Abstract
A metal-free Cs2CO3-promoted hydrothiolation of alkynes with aryl thioureas for stereoselective synthesis of (Z)-vinyl sulfides has been reported. Vinyl thioethers were obtained without a metal catalyst in good yields via anti-Markovnikov and cis addition. The protocol features a broad substrate scope of the starting materials, high atom economy, good yields, and exclusive stereoselectivity, showing potential synthetic value for the synthesis of a diversity of (Z)-vinyl thioethers.
Topics & Concepts
ChemistryStereoselectivityArylAtom economyCatalysisMarkovnikov's ruleReductive eliminationOrganic chemistryCombinatorial chemistryMedicinal chemistryRegioselectivityAlkylSulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsCyberloafing and Workplace Behavior