Cross-Electrophile Couplings of Benzyl Sulfonium Salts with Thiosulfonates via C–S Bond Activation
Xuan-Bo Hu, Yuwei Chen, Chenlong Zhu, Hao Xu, Xiaocong Zhou, Weidong Rao, Xiao‐Chun Hang, Xue‐Qiang Chu, Zhi‐Liang Shen
Abstract
A zinc-mediated cross-electrophile coupling of benzyl sulfonium salts with thiosulfonates via C-S bond cleavage was achieved. The reductive thiolation proceeded well under transition metal-free conditions to afford the desired benzyl sulfides in good yields, exhibiting both broad substrate scope and good functionality tolerance. In addition, the reaction could be applied to the use of selenosulfonate as an effective selenylation agent and be subjected to scale-up synthesis.
Topics & Concepts
SulfoniumElectrophileChemistrySubstrate (aquarium)Combinatorial chemistryBond cleavageCleavage (geology)ZincMedicinal chemistryPolymer chemistrySalt (chemistry)Organic chemistryCatalysisMaterials scienceComposite materialGeologyFracture (geology)OceanographySulfur-Based Synthesis TechniquesCyberloafing and Workplace BehaviorChemical Synthesis and Reactions