RT Journal Article
T1 Iridium-Catalyzed ortho-Selective Borylation of Aromatic Amides Enabled by 5-Trifluoromethylated Bipyridine Ligands
A1 Marcos-Atanes, Daniel
A1 Vidal Vides, Cristian
A1 Navo Najera, Claudio Daniel
A1 Peccati, Francesca
A1 Jiménez Osés, Gonzalo
A1 Mascareñas Cid, José Luis
AB Iridium-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
PB Wiley
SN 1433-7851
YR 2023
FD 2023
LK http://hdl.handle.net/10347/30384
UL http://hdl.handle.net/10347/30384
LA eng
NO Marcos-Atanes, D., Vidal, C., Navo, C. D., Peccati, F., Jiménez-Osés, G., Mascareñas, J. L., Angew. Chem. Int. Ed. 2023, e202214510; Angew. Chem. 2023, e202214510.
NO Agencia Estatal de Investigación, Ministerio de Ciencia e Innovación. Grant Numbers: PID2019-106184GB-I00, PID2021-125946OB-I00, RTI2018-099592-B-C22, CEX2021-001136-S, SEV-2016-0644, CTQ2016-81797-REDC, FIJC2020-045506-I, IJCI-2017-33168. Consellería de Cultura, Educación e Ordenación Universitaria, Xunta de Galicia. Grant Numbers: 2015-CP082, ED431C-2021/25, 2019-2022, ED431G 2019/03
DS Minerva
RD 28 abr 2026