Transition-metal-free nucleophilic 211At-astatination of spirocyclic aryliodonium ylides

Keitaro Matsuoka; Honoka Obata; Kotaro Nagatsu; Masahiro Kojima; Tatsuhiko Yoshino; Mikako Ogawa; Shigeki Matsunaga

doi:10.1039/D1OB00789K

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Transition-metal-free nucleophilic ²¹¹At-astatination of spirocyclic aryliodonium ylides†

Keitaro Matsuoka,^a Honoka Obata,^ab Kotaro Nagatsu,^b Masahiro Kojima,^a Tatsuhiko Yoshino,

*^a Mikako Ogawa*^ac and Shigeki Matsunaga

*^ac

Author affiliations

* Corresponding authors

^a Faculty of Pharmaceutical Science, Hokkaido University, Sapporo 060-0812, Japan
E-mail: tyoshino@pharm.hokudai.ac.jp, mogawa@pharm.hokudai.ac.jp, smatsuna@pharm.hokudai.ac.jp

^b Department of Advanced Nuclear Medicine Sciences, Institute for Quantum Medical Science, National Institutes for Quantum and Radiological Science and Technology, Chiba, Japan

^c Global Station for Biosurfaces and Drug Discovery, Hokkaido University, Sapporo 060-0812, Japan

Abstract

The transition-metal-free ²¹¹At-astatination of spirocyclic aryliodonium ylides via a nucleophilic aromatic substitution reaction is described. This method enables the preparation of ²¹¹At-radiolabeled compounds derived from multi-functionalized molecules and heteroarenes in good to excellent radiochemical yields.

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

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Article information

DOI: https://doi.org/10.1039/D1OB00789K
Article type: Communication
Submitted: 23 Apr 2021
Accepted: 01 Jun 2021
First published: 04 Jun 2021

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Org. Biomol. Chem., 2021,19, 5525-5528

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Transition-metal-free nucleophilic ²¹¹At-astatination of spirocyclic aryliodonium ylides

K. Matsuoka, H. Obata, K. Nagatsu, M. Kojima, T. Yoshino, M. Ogawa and S. Matsunaga, Org. Biomol. Chem., 2021, 19, 5525 DOI: 10.1039/D1OB00789K

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Organic & Biomolecular Chemistry