Metal- and Base-Free C(sp<sup>2</sup>)–H Arylsulfonylation of Enamides for Synthesis of (<i>E</i>)-β-Amidovinyl Sulfones via the Insertion of Sulfur Dioxide
Lei Chen, Mi Zhou, Lin Shen, X. He, Xiong Li, Xuemei Zhang, Zhong Lian
Abstract
A metal- and base-free C(sp2)–H direct arylsulfonylation of secondary and tertiary enamides with aryldiazonium salts and ex situ generated SO2 (from SOgen) is presented. This method runs smoothly to produce β-amidovinyl sulfones with excellent stereoselectivities in moderate to excellent yields. Moreover, this strategy features good functional group tolerance and environmentally benign reaction conditions. Mechanistic experiments indicate that this sulfonylation may proceed in a radical pathway.
Topics & Concepts
ChemistrySulfurBase (topology)Sulfur dioxideMetalFunctional groupInsertion reactionBase metalCombinatorial chemistryEnvironmentally friendlyOrganic chemistryCatalysisPolymerBiologyMetallurgyEcologyMathematical analysisMathematicsMaterials scienceWeldingSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsChemical Synthesis and Reactions