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Paper | Regular issue | Vol 85, No. 10, 2012, pp.2437-2448
Published online, 21st August, 2012
DOI: 10.3987/COM-12-12533
Suzuki-Miyaura Coupling Reactions of 3,5-Dichloro-1,2,4-thiadiazole

Abdelbasset A. Farahat and David W. Boykin*

*Department of Chemistry, Georgia State University, P.O. Box 4098, Atlanta, Georgia 30302-4098, U.S.A.

Abstract

3,5-Dichloro-1, 2, 4-thiadiazole was allowed to react with different aryl boronic acids under different Suzuki-Miyaura coupling conditions: at room temperature 5-aryl-3-chloro-1, 2, 4-thiadiazoles were obtained and at toluene reflux temperature the products were 3,5-diaryl-1, 2, 4-thiadiazoles. Sequential coupling reactions lead to 3,5-diaryl-1, 2, 4-thiadiazoles with non-identical aryl groups. The structure of 3-methoxy-5-(4-methoxyphenyl) -1, 2, 4-thiadiazole was established from X-ray crystallographic data.