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Paper | Special issue | Vol 88, No. 1, 2014, pp.309-318
Published online, 2nd August, 2013
DOI: 10.3987/COM-13-S(S)17
Synthetic Approaches to 3,3’-Biindolyl and 3,3’-Biindazolyl Derivatives

Azadeh Nakhai and Jan Bergman*

*Department of Biosciences and Nutrition, Unit for Organic Chemistry, Karolinska Institute, Novum Research Park, SE-141 57 Huddinge, Sweden

Abstract

In this paper new syntheses of 3,3’-biindolyl and 3,3’-biindazolyl derivatives are described. Formation of 3,3’-biindolyl derivatives by oxidative coupling of N-acetylindole with TeCl4 gave a good yield, while attempt to use the same reaction conditions for synthesis of 3,3’-biindazolyl derivatives failed. However, conversion of 3-haloindazole derivatives to its trimethylstannane derivative, followed by palladium-catalyzed Stille cross-coupling reaction, resulted in formation of 3,3’-biindazolyl derivatives.