ORGANIC
LETTERS
2011
Vol. 13, No. 13
3478–3481
Ni(II)/Zn Catalyzed Reductive Coupling of
Aryl Halides with Diphenylphosphine
Oxide in Water
Xinghua Zhang,† Huizhi Liu,† Xiaomei Hu,† Guo Tang,*,† Jun Zhu,*,‡ and Yufen Zhao†,§
Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province,
College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005,
Fujian, China, Department of Chemistry and Fujian Provincial Key Laboratory of
Theoretical and Computational Chemistry, College of Chemistry and Chemical
Engineering, Xiamen University, Xiamen 361005, Fujian, China, and Key Laboratory of
Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education),
Department of Chemistry, Tsinghua University, Beijing 100084, China
t12g21@xmu.edu.cn; jun.zhu@xmu.edu.cn
Received May 9, 2011
ABSTRACT
P-Arylation in water has been developed via cross-coupling of aryl halides with diphenylphosphine oxide (Ph2P(O)H) and (RP)-(ꢀ)-menthyl
benzylphosphinate catalyzed by NiCl2 6H2O/Zn under relatively mild conditions.
3
Aromatic organophosphorus compounds have at-
tracted considerable interest due to their wide applications
inorganicsynthesis,1 polymers,2 medicinalchemistry,3 and
photoelectric materials.4 The most frequently employed
method for their preparations is treatment of Ph2P(O)Cl
with Li or Mg aromatics,5 which suffers from a lack of
tolerance for functional groups. The demand for functio-
nalized aromatic phosphine oxides stimulated extensive
studies on PꢀC bond-forming reactions catalyzed by
transition metals,6 e.g., Pd7,8 and Cu,9 but there is still a need
for new methods that involve a cheap and environmentally
† Department of Chemistry and Key Laboratory for Chemical Biology of
Fujian Province, College of Chemistry and Chemical Engineering, Xiamen
University.
‡ Department of Chemistry and Fujian Provincial Key Laboratory of
Theoretical and Computational Chemistry, College of Chemistry and Che-
mical Engineering, Xiamen University.
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§ Tsinghua University.
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r
10.1021/ol201141m
Published on Web 05/27/2011
2011 American Chemical Society