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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.

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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… Click to show full 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.

Keywords: ipso cyclization; sulfonated spiro; sulfonylation ipso; visible light; spiro trienones; light promoted

Journal Title: Chemical communications
Year Published: 2019

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