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Site-Selective Aerobic C-H Monoacylation of Carbazoles Using Palladium Catalysis.

ABSTRACT: This manuscript describes the development of a remarkably general palladium-catalyzed monoacylation of carbazoles using toluene derivatives playing the dual role of acyl source and organic solvent. The method uses NHPI as the cocatalyst and oxygen as the sole oxidant. Interestingly, the acylation of monosubstituted N-pyridylcarbazoles takes place regioselectively at the C-8 position. The scope of the method is explored using aldehyde as the acyl source. This highly site-selective acylation proceeds through a radical process.

SUBMITTER: Maiti S

PROVIDER: S-EPMC7613175 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature

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Site-Selective Aerobic C-H Monoacylation of Carbazoles Using Palladium Catalysis.

Maiti Subhadip S Mandal Tirtha T Dash Barada Prasanna BP Dash Jyotirmayee J

The Journal of organic chemistry 20201231 2

This manuscript describes the development of a remarkably general palladium-catalyzed monoacylation of carbazoles using toluene derivatives playing the dual role of acyl source and organic solvent. The method uses NHPI as the cocatalyst and oxygen as the sole oxidant. Interestingly, the acylation of monosubstituted <i>N</i>-pyridylcarbazoles takes place regioselectively at the C-8 position. The scope of the method is explored using aldehyde as the acyl source. This highly site-selective acylatio ...[more]

PMID: 33382269

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