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Visible-light promoted one-pot synthesis of sulfonated spiro[4,5]trienones from propiolamides, anilines and sulfur dioxide under transition metal-free conditions†
Yu Liu,Qiao-Lin Wang,Zan Chen,Quan Zhou,Bi-Quan Xiong,Pan-Liang Zhang,Ke-Wen Tang
Chemical Communications Pub Date : 09/14/2019 00:00:00 , DOI:10.1039/C9CC05949K
Abstract

A novel visible-light promoted sulfonylation/ipso-cyclization of N-arylpropiolamides with arylamines and DABCO·(SO2)2 to synthesize various sulfonated spiro[4,5]trienones is reported. This sulfonylation/ipso-cyclization reaction proceeds via a radical process and undergoes arylsulfonyl radical formation, sulfonylation, and ipso-cyclization. The experimental results indicate that H2O provides an oxygen atom for the construction of the carbonyl group.

Graphical abstract: Visible-light promoted one-pot synthesis of sulfonated spiro[4,5]trienones from propiolamides, anilines and sulfur dioxide under transition metal-free conditions
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