Visible-light promoted cascade cyanoalkylsulfonylation/ipso-cyclization of N-arylpropiolamides toward sulfonated spiro[4,5]trienones via SO2 insertion

A novel visible-light induced sulfonylation/ipso-cyclization of N-arylpropiolamides with cyclobutanone oxime esters and Na2S2O5 was reported. This protocol proceeded via a radical process. The wide substrate scope, sustainable metal-free conditions and readily accessible reagents make this protocol...

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Published in:Organic & biomolecular chemistry 2023-06, Vol.21 (23), p.4823-4832
Main Authors: Shan, Xiwen, Gao, Yu, Lu, Yaru, Huang, Rong, Sun, Tengteng, Lu, Kui, Zhao, Xia
Format: Article
Language:English
Subjects:
Esters
Oxime esters
Reagents
Sodium metabisulfite
Substrates
Sulfur dioxide
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container_issue 23
container_start_page 4823
container_title Organic & biomolecular chemistry
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creator Shan, Xiwen
Gao, Yu
Lu, Yaru
Huang, Rong
Sun, Tengteng
Lu, Kui
Zhao, Xia
description A novel visible-light induced sulfonylation/ipso-cyclization of N-arylpropiolamides with cyclobutanone oxime esters and Na2S2O5 was reported. This protocol proceeded via a radical process. The wide substrate scope, sustainable metal-free conditions and readily accessible reagents make this protocol an efficient and green strategy for the synthesis of cyanoalkyl sulfonated spiro[4,5]trienones.
doi_str_mv 10.1039/d3ob00557g
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subjects Esters
Oxime esters
Reagents
Sodium metabisulfite
Substrates
Sulfur dioxide
title Visible-light promoted cascade cyanoalkylsulfonylation/ipso-cyclization of N-arylpropiolamides toward sulfonated spiro[4,5]trienones via SO2 insertion
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