| Autor: |
Simon PM; ARC Centre of Excellence in Exciton Science, University of Melbourne, Parkville, Melbourne, Victoria 3010, Australia.; School of Chemistry, Bio21 Institute, University of Melbourne, Parkville, Melbourne, Victoria 3010, Australia., Castillo JO; ARC Centre of Excellence in Exciton Science, University of Melbourne, Parkville, Melbourne, Victoria 3010, Australia.; School of Chemistry, Bio21 Institute, University of Melbourne, Parkville, Melbourne, Victoria 3010, Australia., Owyong TC; ARC Centre of Excellence in Exciton Science, University of Melbourne, Parkville, Melbourne, Victoria 3010, Australia.; School of Chemistry, Bio21 Institute, University of Melbourne, Parkville, Melbourne, Victoria 3010, Australia., White JM; School of Chemistry, Bio21 Institute, University of Melbourne, Parkville, Melbourne, Victoria 3010, Australia., Saker Neto N; ARC Centre of Excellence in Exciton Science, University of Melbourne, Parkville, Melbourne, Victoria 3010, Australia.; School of Chemistry, Bio21 Institute, University of Melbourne, Parkville, Melbourne, Victoria 3010, Australia., Wong WWH; ARC Centre of Excellence in Exciton Science, University of Melbourne, Parkville, Melbourne, Victoria 3010, Australia.; School of Chemistry, Bio21 Institute, University of Melbourne, Parkville, Melbourne, Victoria 3010, Australia. |
| Abstrakt: |
Boronic acid protecting group chemistry powerfully enhances the versatility of Suzuki-Miyaura cross-coupling. Prominent examples include trifluoroborate salts, N -methyliminodiacetic acid (MIDA) boronates, and 1,8-diaminonaphthalene boronamides. In this work, we present a bis(2-hydroxybenzyl)methylamine (BOMA) ligand that forms tridentate complexes with boronic acids much like the MIDA ligand but the deprotection is facilitated by organic acids. The BOMA boronates showed considerable stability in both aqueous base and acid, and a variety of chemoselective reactions were performed on these boronates, including selective Suzuki-Miyaura coupling, palladium-catalyzed borylation, ester hydrolysis, alkylation, lithiation-borylation, and oxidative hydroxydeboronation. |
