P-directed borylation of phenols.

Clément Cazorla, Timothy S De Vries, Edwin Vedejs

Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.

Organic letters 2013 Mar 1

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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.