Palladium(ii)-mediated rapid 11C-cyanation of (hetero)arylborons

Zhouen Zhang; Takashi Niwa; Yasuyoshi Watanabe; Takamitsu Hosoya

doi:10.1039/c8ob02049c

Palladium(ii)-mediated rapid ¹¹C-cyanation of (hetero)arylborons

Org Biomol Chem. 2018 Nov 7;16(41):7711-7716. doi: 10.1039/c8ob02049c. Epub 2018 Oct 5.

Authors

Zhouen Zhang¹, Takashi Niwa¹, Yasuyoshi Watanabe¹, Takamitsu Hosoya²

Affiliations

¹ 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. zhang.zhouen@riken.jp takamitsu.hosoya@riken.jp.
² 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. zhang.zhouen@riken.jp takamitsu.hosoya@riken.jp 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.

PMID: 30288522
DOI: 10.1039/c8ob02049c

Abstract

A palladium(ii)-mediated rapid ¹¹C-cyanation of (hetero)arylborons with [¹¹C]NH₄CN/NH₃ 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 [¹¹C]cyanoarenes, including PET tracers for aromatase imaging. A mechanistic study of the ¹¹C-cyanation suggests the instantaneous formation of a mono[¹¹C]cyanopalladium(ii) complex that reacts smoothly with arylborons.

Publication types

Research Support, Non-U.S. Gov't