Catalytic Enantioselective α-Fluorination of 2-Acyl Imidazoles via Iridium Complexes

Guo-Qiang Xu; Hui Liang; Jie Fang; Zhi-Long Jia; Jian-Qiang Chen; Peng-Fei Xu

doi:10.1002/asia.201601306

Catalytic Enantioselective α-Fluorination of 2-Acyl Imidazoles via Iridium Complexes

Chem Asian J. 2016 Dec 6;11(23):3355-3358. doi: 10.1002/asia.201601306. Epub 2016 Nov 10.

Authors

Guo-Qiang Xu¹, Hui Liang¹, Jie Fang¹, Zhi-Long Jia¹, Jian-Qiang Chen¹, Peng-Fei Xu¹

Affiliation

¹ State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, P.R. China.

PMID: 27790869
DOI: 10.1002/asia.201601306

Abstract

The first highly enantioselective α-fluorination of 2-acyl imidazoles utilizing iridium catalysis has been accomplished. This transformation features mild conditions and a remarkably broad substrate scope, providing an efficient and highly enantioselective approach to obtain a wide range of fluorine-containing 2-acyl imidazoles which are found in a variety of bioactive compounds and prodrugs. A large scale synthesis has also been tested to demonstrate the potential utility of this fluorination method.

Keywords: 2-acyl imidazoles; asymmetric catalysis; enantioselectivity; fluorination; iridium.