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Palladium(ii)-mediated rapid C-cyanation of (hetero)arylborons. | LitMetric
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Palladium(ii)-mediated rapid C-cyanation of (hetero)arylborons.

Zhouen Zhang Takashi Niwa Yasuyoshi Watanabe Takamitsu Hosoya

Org Biomol Chem

Chemical Biology Team, Division of Bio-Function Dynamics Imaging, RIKEN Center for Life Science Technologies (CLST) and Laboratory for Chemical Biology, RIKEN Center for Biosystems Dynamics Research (BDR), 6-7-3 Minatojima-minamimachi, Chuo-ku, Kobe 650-0047, Japan. and Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan.

Published: November 2018

A palladium(ii)-mediated rapid C-cyanation of (hetero)arylborons with [C]NHCN/NH has been developed using bench-stable and readily available reagents. The method showed excellent functional-group tolerance, and allowed the highly efficient synthesis of a wide range of [C]cyanoarenes, including PET tracers for aromatase imaging. A mechanistic study of the C-cyanation suggests the instantaneous formation of a mono[C]cyanopalladium(ii) complex that reacts smoothly with arylborons.

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http://dx.doi.org/10.1039/c8ob02049cDOI Listing

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