Issue 16, 2003

Regiospecific Suzuki coupling of 3,5-dichloroisothiazole-4-carbonitrile

Abstract

3,5-Dichloroisothiazole-4-carbonitrile 1 reacts with aryl- and methylboronic acids to give in high yields the 3-chloro-5-(aryl and methyl)-isothiazole-4-carbonitrile 2 regiospecifically. The reaction was optimized with respect to base, phase transfer agent and palladium catalyst. Suzuki coupling at C-5 was also achieved in high yield using potassium phenyltrifluoroborate. The regiospecificity of either coupling method is maintained with 3,5-dibromoisothiazole-4-carbonitrile 4 to give exclusively 3-bromo-5-phenylisothiazole-4-carbonitrile 5. Suzuki cross-coupling conditions applied to 3-chloro-5-phenylisothiazole-4-carbonitrile 2a gave 3-phenoxy-5-phenylisothiazole-4-carbonitrile 6, which was prepared independently, and not the 3-phenyl derivative. All isothiazole products were fully characterized.

Graphical abstract: Regiospecific Suzuki coupling of 3,5-dichloroisothiazole-4-carbonitrile

Article information

Article type
Paper
Submitted
29 May 2003
Accepted
30 Jun 2003
First published
14 Jul 2003

Org. Biomol. Chem., 2003,1, 2900-2907

Regiospecific Suzuki coupling of 3,5-dichloroisothiazole-4-carbonitrile

I. C. Christoforou, P. A. Koutentis and C. W. Rees, Org. Biomol. Chem., 2003, 1, 2900 DOI: 10.1039/B306005E

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