Photo-Driven Regiodivergent Arylation/Cyclization and Arylation/Hydroxylation of <i>N</i>-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(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> cocatalyzed radical cascade arylation/cyclization of <i>N</i>-alkyl-<i>N</i>-arylmethacrylamides can obtain functionalized 3,3-disubstituted oxindoles with the assistance of photocatalyst eosin Y-Na<sub>2</sub>. In the absence of any catalyst, with purple light irradiation and electron-donor-acceptor (EDA) complex initiation, the radical cascade arylation/hydroxylation of <i>N</i>-arylmethacrylamides affords α-hydroxylamides. This methodology highlights the arts in accessing different regioisomers by altering the substrates and photocatalytic strategies.
Authors
- Azhar Iqbal (ORCID: https://orcid.org/0000-0002-5221-9384)
- Xinlei Zhou
- Weiwei Jin (ORCID: https://orcid.org/0000-0002-5996-3229)
- Chenjiang Liu (ORCID: https://orcid.org/0000-0002-8241-0809)
- Ziren Chen (ORCID: https://orcid.org/0000-0002-3298-9584)
- Bin Wang (ORCID: https://orcid.org/0000-0002-8755-6401)
- Yonghong Zhang (ORCID: https://orcid.org/0000-0002-7740-9408)
- Yu Xia (ORCID: https://orcid.org/0000-0002-0591-9169)
- Wei Xu
Institutions
- Bacha Khan University (PK)
- Xinjiang University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-08-21
- DOI
- https://doi.org/10.1021/acs.joc.4c01492
- Citations
- 12
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 3.00
Funders
- Natural Science Foundation of Xinjiang Province
- National Natural Science Foundation of China