Affiliation:
1. Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) and Departamento de Química Orgánica Universidade de Santiago de Compostela 15782 Santiago de Compostela A Coruña Spain
2. CIC bioGUNE Basque Research and Technology Alliance BRTA Bizkaia Technology Park 48162 Derio Spain
3. Ikerbasque Basque Foundation for Science 48013 Bilbao Spain
Abstract
AbstractIridium‐catalyzed borylations of aromatic C−H bonds are highly attractive transformations because of the diversification possibilities offered by the resulting boronates. These transformations are best carried out using bidentate bipyridine or phenanthroline ligands, and tend to be governed by steric factors, therefore resulting in the competitive functionalization of meta and/or para positions. We have now discovered that a subtle change in the bipyridine ligand, namely, the introduction of a CF3 substituent at position 5, enables a complete change of regioselectivity in the borylation of aromatic amides, allowing the synthesis of a wide variety of ortho‐borylated derivatives. Importantly, thorough computational studies suggest that the exquisite regio‐ and chemoselectivity stems from unusual outer‐sphere interactions between the amide group of the substrate and the CF3‐substituted aryl ring of the bipyridine ligand.
Funder
Ministerio de Ciencia e Innovación
Consellería de Cultura, Educación e Ordenación Universitaria, Xunta de Galicia
H2020 European Research Council
Ministerio de Educación, Cultura y Deporte
Cited by
1 articles.
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