TCT-Mediated and Water-Controlled Synthesis of Benzofuran-3(2H)-ones Bearing a Quaternary Carbon Center via a Radical Process Using Dimethyl Sulfoxide as a Dual Synthon

• DOI: 10.1021/acs.joc.5c00201
• Publication Date: 2025-04-10T12:18:02Z
• Authors: Qing Chen; Zhao Du; Chuanqi Liu; Xiaoqian Wang; Wantong Yue; Yilei Wang; Zhihua Peng
• Keywords: Synthon; Benzofuran; Quaternary carbon; Center (category theory); Sulfoxide; Dual role

An efficient and attractive method for the synthesis of valuable benzofuran-3(2H)-one derivatives bearing a quaternary center in one step by employing dimethyl sulfoxide (DMSO) as dual synthon under metal-free conditions has been developed. In this reaction, DMSO activated cyanuric chloride (TCT) provides two different units (CH3 SMe) target molecules, construction carbon benzofuran-3(2H)-ones can be controlled addition water. Furthermore, functional group compatibility synthetic value were demonstrated scope evaluation gram-scale experiments. The mechanistic studies show that reaction may proceed via radical process.