Directing-Group-Assisted C(sp<sup>2</sup>)–H Arylsulfonylation from Sulfur Dioxide
Tong‐Hao Zhu, Jie Wu
Abstract
A straightforward and stereoselective preparation of (Z)-β-alkenyl sulfones through a reaction of N-tosyl acrylamides, 1,4-diazabicyclo[2.2.2]octane-sulfur dioxide, and aryldiazonium tetrafluoroborates under copper catalysis is accomplished. The direct C(sp2)–H arylsulfonylation of acrylamides using sulfur dioxide as the sulfonyl source in the presence of copper trifluoroacetate proceeds smoothly, giving rise to (Z)-β-alkenyl sulfones in good yields. During the reaction process, excellent regio- and stereoselectivities are observed.
Topics & Concepts
ChemistrySulfur dioxideGroup (periodic table)SulfurMedicinal chemistryOrganic chemistrySulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsChemical Synthesis and Reactions