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Remote Regioselective Electrophilic Aromatic Substitutions Using a Tetrafluoropyridyl (TFP) Phenol Protecting Group

preprint
submitted on 10.10.2019, 12:10 and posted on 16.10.2019, 05:56 by William Brittain, Steven Cobb

Herein, we report the development of remote regioselective electrophilic aromatic substitution reactions enabled by the tetrafluoropyridyl (TFP) protecting group. The TFP group significantly reduces the reactivity of the aromatic ring to which it is attached allowing for substitution selectivity on non-TFP protected rings and in turn access to unsymmetric multi-aryl systems. Yields of the unsymmetric multi-aryl systems ranged between 58-96%. In addition, we disclose that through sequential reactions and protection/deprotection of the TFP group, substitution patterns which do not conform to classical regioselectivity rules can be readily accessed.

Funding

Biotechnology and Biological Sciences Research Council [BB/P003656/1]

Durham University’s Medical Research Council Confidence in Concept scheme for financial support [MC-PC-17157].

History

Email Address of Submitting Author

s.l.cobb@durham.ac.uk

Institution

Durham University

Country

United Kingdom

ORCID For Submitting Author

0000-0002-3790-7023

Declaration of Conflict of Interest

No conflicts of interest to declare.

Version Notes

manuscript version 1

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