Protecting Group Controlled Remote Regioselective Electrophilic Aromatic Halogenation Reactions

Brittain, William David George; Cobb, Steven L.

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.

Citation

Brittain, W. D. G., & Cobb, S. L. (2020). Protecting Group Controlled Remote Regioselective Electrophilic Aromatic Halogenation Reactions. Journal of Organic Chemistry, 85(11), 6862-6871. https://doi.org/10.1021/acs.joc.9b03322

• Journal Article Type: Article
• Online Publication Date: May 7, 2020
• Publication Date: Jun 5, 2020
• Deposit Date: May 10, 2020
• Publicly Available Date: May 7, 2021
• Journal: Journal of Organic Chemistry
• Print ISSN: 0022-3263
• Electronic ISSN: 1520-6904
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 85
• Issue: 11
• Article Number: 6862-6871
• Pages: 6862-6871
• DOI: https://doi.org/10.1021/acs.joc.9b03322
• Public URL: https://durham-repository.worktribe.com/output/1271100