Photo-Driven Regiodivergent Arylation/Cyclization and Arylation/Hydroxylation of N‑Aryl Methacrylamides with Aryltriazenes: Access to Functionalized 3,3-Disubstituted Oxindoles and α‑Hydroxylamides

A metal-free, light-induced regiodivergent functionalization of α,β-unsaturated amides with aryltriazenes under ambient conditions was developed. The visible light and B­(C6F5)3 cocatalyzed radical cascade arylation/cyclization of N-alkyl-N-arylmethacrylamides can obtain functionalized 3,3-disubstit...

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Published inJournal of organic chemistry Vol. 89; no. 18; pp. 13345 - 13358
Main Authors Zhou, Xinlei, Xu, Wei, Wang, Bin, Iqbal, Azhar, Chen, Ziren, Xia, Yu, Jin, Weiwei, Liu, Chenjiang, Zhang, Yonghong
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 20.09.2024
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Summary:A metal-free, light-induced regiodivergent functionalization of α,β-unsaturated amides with aryltriazenes under ambient conditions was developed. The visible light and B­(C6F5)3 cocatalyzed radical cascade arylation/cyclization of N-alkyl-N-arylmethacrylamides can obtain functionalized 3,3-disubstituted oxindoles with the assistance of photocatalyst eosin Y–Na2. In the absence of any catalyst, with purple light irradiation and electron-donor–acceptor (EDA) complex initiation, the radical cascade arylation/hydroxylation of N-arylmethacrylamides affords α-hydroxylamides. This methodology highlights the arts in accessing different regioisomers by altering the substrates and photocatalytic strategies.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01492