P-directed borylation of phenols

Org Lett. 2013 Mar 1;15(5):984-7. doi: 10.1021/ol303203m. Epub 2013 Jan 30.

Abstract

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.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Boranes / chemical synthesis*
  • Boranes / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Molecular Structure
  • Phenols / chemical synthesis*
  • Phenols / chemistry

Substances

  • Boranes
  • Phenols