Nickel-Catalyzed Direct Cross-Coupling of Diaryl Sulfoxide with Aryl Bromide
Wenxin Li, Bo-Wen Yang, Ying Xuan, Zhuowen Zhang, Xue‐Qiang Chu, Xiaocong Zhou, Mengtao Ma, Zhi‐Liang Shen
Abstract
The direct cross-couplings of diaryl sulfoxides with aryl bromides via C-S bond cleavage could be readily accomplished using nickel(II) as the catalyst, 1,2-bis(diphenylphosphino)ethane (dppe) as the ligand, and magnesium turnings as the reducing metal in THF, leading to the corresponding biaryls in moderate to good yields. The reaction exhibited a broad substrate scope and could be applied to a gram-scale synthesis. The "one-pot" reaction, which avoids the utility of presynthesized and moisture-labile organometallic compounds, is operationally simple and step-economic.
Topics & Concepts
ChemistryArylCatalysisNickelSulfoxideBromideCombinatorial chemistryCoupling reactionMagnesiumReagentLigand (biochemistry)Substrate (aquarium)Bond cleavageMetalVinyl bromideCleavage (geology)Organic chemistryPolymer chemistryAlkylEngineeringGeologyGeotechnical engineeringReceptorOceanographyBiochemistryFracture (geology)Sulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions