2,2'-Biphenols via protecting group-free thermal or microwave-accelerated Suzuki-Miyaura coupling in water

J Org Chem. 2013 Sep 6;78(17):8680-8. doi: 10.1021/jo401398n. Epub 2013 Aug 13.

Abstract

User-friendly protocols for the protecting group-free synthesis of 2,2'-biphenols via Suzuki-Miyaura coupling of o-halophenols and o-boronophenol are presented. The reactions proceed in water in the presence of simple additives such as K2CO3, KOH, KF, or TBAF and with commercially available Pd/C as precatalyst. Expensive or laboriously synthesized ligands or other additives are not required. In the case of bromophenols, efficient rate acceleration and short reaction times were accomplished by microwave irradiation.

MeSH terms

  • Microwaves*
  • Molecular Structure
  • Phenols / chemical synthesis*
  • Phenols / chemistry
  • Temperature*
  • Water / chemistry*

Substances

  • Phenols
  • Water
  • 2,2'-biphenol