Synlett 2016; 27(07): 1091-1095
DOI: 10.1055/s-0035-1561317
letter
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Direct Arylation of 2,6-Disubstituted Imidazo[2,1-b][1,3,4]thiadiazoles

Chloé Copin
Institut de Chimie Organique et Analytique, ICOA, Univ Orleans, UMR 7311 CNRS, Rue de Chartres, BP 6759, 45067 Orleans, France   Email: sylvain.routier@univ-orleans.fr
,
Nicolas Henry
Institut de Chimie Organique et Analytique, ICOA, Univ Orleans, UMR 7311 CNRS, Rue de Chartres, BP 6759, 45067 Orleans, France   Email: sylvain.routier@univ-orleans.fr
,
Frédéric Buron
Institut de Chimie Organique et Analytique, ICOA, Univ Orleans, UMR 7311 CNRS, Rue de Chartres, BP 6759, 45067 Orleans, France   Email: sylvain.routier@univ-orleans.fr
,
Sylvain Routier*
Institut de Chimie Organique et Analytique, ICOA, Univ Orleans, UMR 7311 CNRS, Rue de Chartres, BP 6759, 45067 Orleans, France   Email: sylvain.routier@univ-orleans.fr
› Author Affiliations
Further Information

Publication History

Received: 18 November 2015

Accepted after revision: 14 December 2015

Publication Date:
08 January 2016 (online)


Preview

Abstract

This work reports the original synthesis of trisarylimidazo[2,1-b][1,3,4]thiadiazole derivatives using a C–H arylation process. The scope of the reaction demonstrated the critical importance of the electronic effects of each substituent on the efficiency of the reaction. In addition, a double efficient ‘one-pot’ functionalization at the C-2 and then at the C-5 positions of 2-bromo-6-arylimidazo[2,1-b][1,3,4]thiadiazole derivatives was achieved using a sequential Suzuki–Miyaura–C–H arylation cascade procedure.

Supporting Information