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Base-Catalyzed Aryl Halide Isomerization Enables the 4-Selective Substitution of 3-Bromopyridines

preprint
submitted on 24.03.2020 and posted on 25.03.2020 by Thomas R. Puleo, Jeffrey Bandar
The base-catalyzed isomerization of simple aryl halides is presented and utilized to achieve the 4-selective etherification, hydroxylation and amination of 3bromopyridines. Mechanistic studies support isomerization of 3-bromopyridines to 4-bromopyridines proceeds via pyridyne intermediates and that 4-substitution selectivity is driven by a facile SNAr reaction. Beneficial aspects of a tandem aryl halide isomerization/selective interception approach to aromatic functionalization are demonstrated.

Funding

American Chemical Society Petroleum Research Fund #60171-DNI1

Colorado State University

History

Email Address of Submitting Author

jeff.bandar@colostate.edu

Institution

Colorado State University

Country

United States

ORCID For Submitting Author

0000-0001-5418-3082

Declaration of Conflict of Interest

The authors declare no competing financial interest.

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