4.3 Article

Pd-Catalyzed P-Arylation of Triarylantimony Dicarboxylates with Dialkyl H-Phosphites without a Base: Synthesis of Arylphosphonates

Journal

CHEMICAL & PHARMACEUTICAL BULLETIN
Volume 63, Issue 2, Pages 130-133

Publisher

PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.c14-00727

Keywords

Hirao-type P-arylation; triarylantimony diacetate; arylphosphonate; dialkyl H-phosphite; base-free reaction

Funding

  1. Ministry Education, Culture, Sports, Sciences and Technology of Japan
  2. Institute of Pharmaceutical Life Sciences
  3. Aichi Gakuin University
  4. Hokuriku University

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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.

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