P-directed borylation of phenols.
Internal borylation occurs upon activation of aryl di-isopropylphosphinite boranes with HNTf(2) to give heterocyclic intermediates that can be reductively quenched to afford 6 or treated with KHF(2) to give the phenolic potassium aryl trifluoroborate salts 10. The latter salts are useful for Pd-catalyzed coupling with aryl iodides under Molander conditions, provided that precautions are taken to remove the KNTf(2) byproduct from the preceding KHF(2) step.
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Clément
C
Cazorla
Timothy S
TS
De Vries
Edwin
E
Vedejs
D001880:Boranes / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry
D001880:Boranes; D010636:Phenols