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

Mio Matsumura; Yuqiang Dong; Naoki Kakusawa; Shuji Yasuike

doi:10.1248/cpb.c14-00727

Notes

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

Mio Matsumura, Yuqiang Dong, Naoki Kakusawa, Shuji Yasuike

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Keywords: Hirao-type P-arylation, triarylantimony diacetate, arylphosphonate, dialkyl H-phosphite, base-free reaction

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2015 Volume 63 Issue 2 Pages 130-133

DOI https://doi.org/10.1248/cpb.c14-00727

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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.

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