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Literature DB >> 22120821

Synthesis of oxindoles via visible light photoredox catalysis.

Xuhui Ju¹, Yan Liang, Pingjing Jia, Weifei Li, Wei Yu.

Abstract

2-Electron-withdrawing-group-substituted 2-bromoanilides can be converted to the corresponding 3,3-disubstituted oxindoles with high efficiency under visible light irradiation by using fac-Ir(ppy)(3) as the photoredox catalyst. This protocol is suitable for the synthesis of oxindoles with chloro and bromo atoms attached to the phenyl ring.

Entities: Chemical Gene

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Year: 2011 PMID： 22120821 DOI： 10.1039/c1ob06652h

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

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Cited

7 in total

Review 1. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors: Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal: Chem Rev Date: 2013-03-19 Impact factor: 60.622

Review 2. The Fascinating Chemistry of α-Haloamides.

Authors: Anna Fantinati; Vinicio Zanirato; Paolo Marchetti; Claudio Trapella
Journal: ChemistryOpen Date: 2020-01-13 Impact factor: 2.911

3. Eosin Y-catalyzed visible-light-mediated aerobic oxidative cyclization of N,N-dimethylanilines with maleimides.

Authors: Zhongwei Liang; Song Xu; Wenyan Tian; Ronghua Zhang
Journal: Beilstein J Org Chem Date: 2015-04-01 Impact factor: 2.883

4. Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp(2) C-H and sp(3) C-H bonds.

Authors: Nivesh Kumar; Santanu Ghosh; Subhajit Bhunia; Alakesh Bisai
Journal: Beilstein J Org Chem Date: 2016-06-08 Impact factor: 2.883

Synthesis of oxindoles via visible light photoredox catalysis.

Review 1. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Review 2. The Fascinating Chemistry of α-Haloamides.

3. Eosin Y-catalyzed visible-light-mediated aerobic oxidative cyclization of N,N-dimethylanilines with maleimides.

4. Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp(2) C-H and sp(3) C-H bonds.

5. Ligand functionalization as a deactivation pathway in a fac-Ir(ppy)₃-mediated radical addition.

6. Oxindole synthesis via polar-radical crossover of ketene-derived amide enolates in a formal [3 + 2] cycloaddition.

Review 7. Activation modes in biocatalytic radical cyclization reactions.

Synthesis of oxindoles via visible light photoredox catalysis.

Review 1. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Review 2. The Fascinating Chemistry of α-Haloamides.

3. Eosin Y-catalyzed visible-light-mediated aerobic oxidative cyclization of N,N-dimethylanilines with maleimides.

4. Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp(2) C-H and sp(3) C-H bonds.

5. Ligand functionalization as a deactivation pathway in a fac-Ir(ppy)3-mediated radical addition.

6. Oxindole synthesis via polar-radical crossover of ketene-derived amide enolates in a formal [3 + 2] cycloaddition.

Review 7. Activation modes in biocatalytic radical cyclization reactions.

5. Ligand functionalization as a deactivation pathway in a fac-Ir(ppy)₃-mediated radical addition.