Open AccessSite-Selective Aerobic C–H Monoacylation of Carbazoles Using Palladium Catalysis
Author(s) -
Subhadip Maiti,
Tirtha Mandal,
Barsha Dash,
Jyotirmayee Dash
Publication year - 2020
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.0c01746
Subject(s) - acylation , palladium , aldehyde , chemistry , catalysis , toluene , solvent , organic chemistry , dual role , regioselectivity , combinatorial chemistry
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.