Regioselective oxidative trifluoromethylation of imidazoheterocycles via C(sp2)-H bond functionalization

Kamarul Monir; Avik Kumar Bagdi; Monoranjan Ghosh; Alakananda Hajra

doi:10.1021/jo502928e

Regioselective oxidative trifluoromethylation of imidazoheterocycles via C(sp2)-H bond functionalization

J Org Chem. 2015 Feb 6;80(3):1332-7. doi: 10.1021/jo502928e. Epub 2015 Jan 26.

Authors

Kamarul Monir¹, Avik Kumar Bagdi, Monoranjan Ghosh, Alakananda Hajra

Affiliation

¹ Department of Chemistry, Visva-Bharati (A Central University) , Santiniketan 731235, India.

PMID: 25615451
DOI: 10.1021/jo502928e

Abstract

Catalytic oxidative trifluoromethylation of imidazopyridines has been carried out at room temperature through the functionalization of the sp(2) C-H bond employing Langlois reagent under ambient air. A library of 3-(trifluoromethyl)imidazo[1,2-a]pyridines with broad functionalities have been synthesized regioselectively. This methodology is also applicable to imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Hydrogen Bonding
Imidazoles / chemical synthesis*
Imidazoles / chemistry*
Methylation
Molecular Structure
Oxidation-Reduction
Pyridines / chemical synthesis*
Pyridines / chemistry*
Stereoisomerism
Thiazoles / chemical synthesis*
Thiazoles / chemistry*

Substances

Imidazoles
Pyridines
Thiazoles
benzo(d)imidazo(2,1-b)thiazole
imidazo(2,1-b)thiazole