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Angew Chem Int Ed Engl. 2019 Sep 9;58(37):13039-13043. doi: 10.1002/anie.201907366. Epub 2019 Jul 17.

Hydrogen Bond Directed ortho-Selective C-H Borylation of Secondary Aromatic Amides.

Author information

1
Supramolecular and Homogeneous Catalysis Group, Van't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Science Park 904, 1098 XH, Amsterdam, The Netherlands.

Abstract

Reported is an iridium catalyst for ortho-selective C-H borylation of challenging secondary aromatic amide substrates, and the regioselectivity is controlled by hydrogen-bond interactions. The BAIPy-Ir catalyst forms three hydrogen bonds with the substrate during the crucial activation step, and allows ortho-C-H borylation with high selectivity. The catalyst displays unprecedented ortho selectivities for a wide variety of substrates that differ in electronic and steric properties, and the catalyst tolerates various functional groups. The regioselective C-H borylation catalyst is readily accessible and converts substrates on gram scale with high selectivity and conversion.

KEYWORDS:

C−H activation; borylation; hydrogen bonds; iridium; supramolecular chemistry

PMID:
31237988
DOI:
10.1002/anie.201907366

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