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Isodesmic C-H Borylation: Perspectives and Proof of Concept of Transfer Borylation Catalysis

preprint
submitted on 16.11.2018 and posted on 19.11.2018 by Etienne Rochette, Frédéric-Georges Fontaine
The potential advantages of using arylboronic acids
or esters as boron source in the C-H borylation are discussed. The
concept is showcased by using commercially available and air-stable
2-mercaptopyridine as a metal-free catalyst for the transfer
borylation of heteroarenes, using furylboronic acid catechol ester
as the borylation agent. The catalysis can be performed in air using
unpurified solvent and shows a unique functional group tolerance
among C-H borylation reactions, tolerating notably alkene and alkyne
functional groups. The computational investigation of the
mechanism is also described.

History

Email Address of Submitting Author

etienne.rochette.2@ulaval.ca

Institution

Université Laval

Country

Canada

ORCID For Submitting Author

0000-0003-2974-8701

Declaration of Conflict of Interest

The authors declare no competing financial interests.

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in Journal of the American Chemical Society

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