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Synthesis 2008(21): 3473-3477  
DOI: 10.1055/s-0028-1083155
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Copper-Catalyzed Coupling of 2-Haloacetanilides with Phosphine Oxides and Phosphites under Mild Conditions

Deshou Jianga, Qun Jiangb, Hua Fu*a, Yuyang Jianga,b, Yufen Zhaoa
a Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China
Fax: +86(10)62781695; e-Mail: fuhua@mail.tsinghua.edu.cn ;
b Key Laboratory of Chemical Biology (Guangdong Province), Graduate School of Shenzhen, Tsinghua University, Shenzhen 518057, P. R. of China
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Publication History

Received 14 May 2008
Publication Date:
25 September 2008 (online)

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Abstract

We have developed a highly efficient method for the copper-catalyzed coupling of 2-haloacetanilides with phosphine oxides­ and phosphites in the presence of a catalytic amount of copper(I) iodide and N-methylpyrrolidine-2-carboxamide under mild conditions (45-55 ˚C); the P-arylation products were synthesized in good to excellent yields in short times using 2-bromotrifluoroacetanilides and 2-iodotrifluoroacetanilides as the starting materials. This represents the lowest reaction temperatures for copper-catalyzed P-arylation thus far.

Key words

Ullmann reaction - P-arylation - ortho effect - copper catalysis­ - N,N-ligand

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