Selenium Radical Mediated Cascade Cyclization: Concise Synthesis of Selenated Benzofurans (Benzothiophenes)

• DOI: 10.1021/acs.orglett.9b02315
• Publication Date: 2019-08-13T11:57:21Z
• Authors: Cui An; Chen-Yuan Li; Xiao-Bo Huang; Wen-Xia Gao; Yun-Bing Zhou; Miao-Chang Liu; Hua-Yue Wu
• Keywords: Radical cyclization

Presented in this work is a novel methodology for the synthesis of selenated benzofurans (or benzothiophenes) via AgNO2-catalyzed radical cyclization 2-alkynylanisoles 2-alkynylthioanisoles), Se powder, and arylboronic acids. This method enables construction benzofuran (benzothiophene) ring, two C–Se bonds, C–O(S) bond as well cleavage single step. Preliminary mechanistic studies imply that proceeds an aryl selenium intermediate.