PhI(OAc)2/KI-mediated reaction of aryl sulfinates with alkenes, alkynes, and α,β-unsaturated carbonyl compounds: Synthesis of vinyl sulfones and β-iodovinyl sulfones

Abstract

(Diacetoxyiodo)benzene [PhI(OAc)2, DIB] was able to promote the reaction of sodium aryl sulfinate and potassiumiodide (KI) with alkenes and alkynes to afford the corresponding vinyl sulfones and β-iodovinyl sulfones, respectively, in good yields. The salient features of this reaction are that it employs a commercially available and environmentally benign hypervalent iodine(III) reagent, a one-step reaction, a short reaction time, and mild reaction conditions. (Diacetoxyiodo)benzene/KI was able to promote the reaction of sodium aryl sulfinates with alkenes to afford vinyl sulfones in good yields. Alkynes underwent a similar reaction to give β-iodovinyl sulfones. The present method can be considered to be a convenient and attractive alternative to the existing methods for the synthesis of these intermediates, which are important in organic chemistry. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.