Synthesis of 18F-difluoromethylarenes using aryl boronic acids, ethyl bromofluoroacetate and [18F]fluoride

Jeroen B. I. Sap; Thomas C. Wilson; Choon Wee Kee; Natan J. W. Straathof; Christopher W. am Ende; Paramita Mukherjee; Lei Zhang; Christophe Genicot; Véronique Gouverneur

doi:10.1039/C8SC05096A

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Synthesis of ¹⁸F-difluoromethylarenes using aryl boronic acids, ethyl bromofluoroacetate and [¹⁸F]fluoride†

Jeroen B. I. Sap,^a Thomas C. Wilson,^a Choon Wee Kee,

^a Natan J. W. Straathof,

^a Christopher W. am Ende,^b Paramita Mukherjee,^b Lei Zhang,^b Christophe Genicot^c and Véronique Gouverneur

*^a

Author affiliations

* Corresponding authors

^a Chemistry Research Laboratory, Department of Chemistry, Oxford University, OX1 3TA Oxford, UK
E-mail: veronique.gouverneur@chem.ox.ac.uk
Tel: +44 (0)1865 285002

^b Pfizer Inc., Medicine Design, Eastern Point Road, Groton, Connecticut 06340, and 1 Portland Street, Cambridge, Massachusetts 02139, USA

^c Global Chemistry, UCB New Medicines, UCB Biopharma Sprl, 1420 Braine-L'Alleud, Belgium

Abstract

Herein, we report the radiosynthesis of ¹⁸F-difluoromethylarenes via the assembly of three components, a boron reagent, ethyl bromofluoroacetate, and cyclotron-produced non-carrier added [¹⁸F]fluoride. The two key steps are a copper-catalysed cross-coupling reaction, and a Mn-mediated ¹⁸F-fluorodecarboxylation.

This article is part of the themed collections: Most popular 2019-2020 organic chemistry articles, New reactivity in organic chemistry and Editor's choice - Paolo Melchiorre

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Article information

DOI: https://doi.org/10.1039/C8SC05096A
Article type: Edge Article
Submitted: 15 Nov. 2018
Accepted: 28 Janv. 2019
First published: 29 Janv. 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2019,10, 3237-3241

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Synthesis of ¹⁸F-difluoromethylarenes using aryl boronic acids, ethyl bromofluoroacetate and [¹⁸F]fluoride

J. B. I. Sap, T. C. Wilson, C. W. Kee, N. J. W. Straathof, C. W. A. Ende, P. Mukherjee, L. Zhang, C. Genicot and V. Gouverneur, Chem. Sci., 2019, 10, 3237 DOI: 10.1039/C8SC05096A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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