Sulfoxide synthesis from sulfinate esters under Pummerer-like conditions
Akihiro Kobayashi, Tsubasa Matsuzawa, Takamitsu Hosoya, Suguru Yoshida
Abstract
A facile synthetic method for the preparation of allyl sulfoxides by S-allylation of sulfinate esters proceeds through sulfonium intermediates without [3,3]-sigmatropic rearrangement and further Pummerer-type reactions of the resulting allyl sulfoxides. On the basis of the plausible reaction mechanism involving sulfonium salt intermediates, S-alkynylation and S-arylation were also accomplished.
Topics & Concepts
SulfoniumSulfoxidePummerer rearrangementChemistrySulfoneSigmatropic reactionSalt (chemistry)Organic chemistryCatalysisAcetic anhydrideSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsOrganic and Inorganic Chemical Reactions