Proline/pipecolinic acid-promoted copper-catalyzed P-arylation

Cheng Huang; Xu Tang; Hua Fu; Yuyang Jiang; Yufen Zhao

doi:10.1021/jo060492j

Proline/pipecolinic acid-promoted copper-catalyzed P-arylation

J Org Chem. 2006 Jun 23;71(13):5020-2. doi: 10.1021/jo060492j.

Authors

Cheng Huang¹, Xu Tang, Hua Fu, Yuyang Jiang, Yufen Zhao

Affiliation

¹ Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, PR China.

PMID: 16776539
DOI: 10.1021/jo060492j

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkylation
Catalysis
Copper / chemistry*
Hydrocarbons, Halogenated / chemistry
Iodides / chemistry*
Molecular Structure
Organophosphorus Compounds / chemical synthesis*
Organophosphorus Compounds / chemistry
Pipecolic Acids / chemistry*
Proline / chemistry*
Stereoisomerism

Substances

Hydrocarbons, Halogenated
Iodides
Organophosphorus Compounds
Pipecolic Acids
Copper
cuprous iodide
Proline