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Proline/Pipecolinic Acid-Promoted Copper-Catalyzed P-Arylation

Cheng Huang,^† Xu Tang,^† Hua Fu,*^† Yuyang Jiang,^†^‡ and Yufen Zhao^†

Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China, and Key Laboratory of Chemical Biology, Guangdong Province, Graduate School of Shenzhen, Tsinghua University, Shenzhen 518057, P. R. China fuhua@mail.tsinghua.edu.cn

J. Org. Chem., 2006, 71 (13), pp 5020–5022

DOI: 10.1021/jo060492j

Publication Date (Web): May 27, 2006

†

Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology.

To whom correspondence should be addressed. Fax: (+86) 10-62781695.

‡

Key Laboratory of Chemical Biology.

Abstract

We have developed a convenient and efficient approach for P-arylation of organophosphorus compounds containing P−H. Using commercially available and inexpensive proline and pipecolinic acid as the ligands greatly improved the efficiency of the coupling reactions, so the method can provide an entry to arylphosphonates, arylphosphinates and arylphosphine oxides.

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Published In Issue June 23, 2006
Received March 7, 2006

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Proline/Pipecolinic Acid-Promoted Copper-Catalyzed P-Arylation