Issue 50, 2018

Regioselective C–H alkenylation of imidazoles and its application to the synthesis of unsymmetrically substituted benzimidazoles

Abstract

A palladium-catalyzed C–H alkenylation of imidazoles has been developed. High C5 selectivity was achieved for C2-unsubstituted and C2-substituted imidazoles using oxygen and copper(II) acetate, respectively, as oxidants. The obtained products were applied to benzannulation through a sequence involving transposition of N-alkyl groups to give C4-alkenyl imidazoles, alkenylation, thermal 6π-electrocyclization, and oxidation, affording unsymmetrically substituted benzimidazoles.

Graphical abstract: Regioselective C–H alkenylation of imidazoles and its application to the synthesis of unsymmetrically substituted benzimidazoles

Supplementary files

Article information

Article type
Communication
Submitted
26 mar 2018
Accepted
08 may 2018
First published
09 may 2018

Chem. Commun., 2018,54, 6879-6882

Regioselective C–H alkenylation of imidazoles and its application to the synthesis of unsymmetrically substituted benzimidazoles

H. Kim, Y. J. Hwang, I. Han and J. M. Joo, Chem. Commun., 2018, 54, 6879 DOI: 10.1039/C8CC02405G

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