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Arylation of Rhodium(II) Azavinyl Carbenes with Boronic Acids

Nicklas Selander, Brady T. Worrell, Stepan Chuprakov, Subash Velaparthi and Valery V. Fokin*

*Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States, Email:

N. Selander, B. T. Worrell, S. Chuprakov, S. Velaparthi, V. V. Fokin, J. Am. Chem. Soc., 2012, 134, 14670-14673.

DOI: 10.1021/ja3062453 (free Supporting Information)


A highly efficient and stereoselective arylation of in situ-generated azavinyl carbenes affords 2,2-diaryl enamines at ambient temperatures. These transition-metal carbenes are directly produced from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of a rhodium carboxylate catalyst. In several cases, the enamines can be cyclized into substituted indoles employing copper catalysis.

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Key Words

Enamines, Indoles

ID: J48-Y2012-2850