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

Zhouen Zhang; Takashi Niwa; Yasuyoshi Watanabe; Takamitsu Hosoya

doi:10.1039/C8OB02049C

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

Zhouen Zhang,*^a Takashi Niwa,

^a Yasuyoshi Watanabe^a and Takamitsu Hosoya

*^ab

Author affiliations

* Corresponding authors

^a 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
E-mail: zhang.zhouen@riken.jp, takamitsu.hosoya@riken.jp

^b 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

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.

This article is part of the themed collection: Synthetic methodology in OBC

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Supplementary files

Supplementary information PDF (3473K)

Article information

DOI: https://doi.org/10.1039/C8OB02049C
Article type: Paper
Submitted: 21 Aug 2018
Accepted: 01 Oct 2018
First published: 02 Oct 2018

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Org. Biomol. Chem., 2018,16, 7711-7716

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

Z. Zhang, T. Niwa, Y. Watanabe and T. Hosoya, Org. Biomol. Chem., 2018, 16, 7711 DOI: 10.1039/C8OB02049C

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Organic & Biomolecular Chemistry