Synthesis of alkynyl sulfides <i>via</i> base-promoted nucleophilic ring-opening of α-bromostyrene sulfonium salt
Junqi Zhou, Ziyu Wang, Hanmiao Xu, Mengke Su, Jian Wen
Abstract
)-S bond cleavage of α-bromostyrene sulfonium salts has been developed. This base-promoted nucleophilic ring-opening pathway allows the preparation of diverse alkynyl sulfide compounds using tetramethylene sulfoxide as the sulfur source. The reaction proceeds with good functional group tolerance and could be applied to the late-stage functionalization of bioactive molecules and drugs. Furthermore, the synthetic utility of this method was demonstrated by a one-pot synthesis, scale-up reaction and further modification of various alkynyl sulfide products.
Topics & Concepts
SulfoniumChemistryNucleophileSulfideCombinatorial chemistrySulfoxideRing (chemistry)SulfurCleavage (geology)Salt (chemistry)Surface modificationBase (topology)Sodium sulfidePolymer chemistryOrganic chemistryMedicinal chemistryCatalysisMaterials scienceMathematical analysisPhysical chemistryComposite materialMathematicsFracture (geology)Sulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions