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Protecting group controlled remote regioselective electrophilic aromatic halogenation reactions.

Brittain, William David George and Cobb, Steven L. (2020) 'Protecting group controlled remote regioselective electrophilic aromatic halogenation reactions.', Journal of organic chemistry., 85 (11). pp. 6862-6871.

Abstract

Being able to utilise a protecting group to influence remote regiocontrol offers a simple alternative approach to direct late-stage functionalisation of complex organic molecules. However, protecting groups that have the ability to influence reaction regioselectivity remote to their local chemical environment are not widely reported in the literature. Herein, we report the development of remote regioselective electrophilic aromatic substitution (SEAr) reactions that are enabled via the application of the tetrafluoropyridyl (TFP) phenol protecting group. We demonstrate that through sequential reactions and protection/deprotection of the TFP group, substitution patterns which do not conform to classical SEAr regioselectivity rules can be readily accessed.

Item Type:Article
Full text:(AM) Accepted Manuscript
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Status:Peer-reviewed
Publisher Web site:https://doi.org/10.1021/acs.joc.9b03322
Publisher statement:This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of organic chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.9b03322
Date accepted:No date available
Date deposited:11 May 2020
Date of first online publication:07 May 2020
Date first made open access:07 May 2021

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