Pd-catalyzed P-arylation of triarylantimony dicarboxylates with dialkyl H-phosphites without a base: synthesis of arylphosphonates

Chem Pharm Bull (Tokyo). 2015;63(2):130-3. doi: 10.1248/cpb.c14-00727.

Abstract

The reaction of triarylantimony diacetates [Ar3Sb(OAc)2] with dialkyl H-phosphites [H-PO(OR)2] in the presence of a Pd(PPh3)4 (5 mol%) catalyst led to the formation of arylphosphonates in moderate to excellent yield under base-free conditions. This reaction is the first example of carbon-phosphorus bond formation by using an organoantimony compound as a pseudo-halide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Coordination Complexes / chemistry
  • Dicarboxylic Acids / chemistry*
  • Palladium / chemistry
  • Phosphites / chemistry*
  • Phosphorous Acids / chemical synthesis
  • Phosphorous Acids / chemistry*

Substances

  • Coordination Complexes
  • Dicarboxylic Acids
  • Phosphites
  • Phosphorous Acids
  • phosphonic acid
  • Palladium