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Ni(II)−(σ-Aryl) Complex: A Facile, Efficient Catalyst for Nickel-Catalyzed Carbon−Nitrogen Coupling Reactions

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Chen Chen^†^‡ and Lian-Ming Yang*^†

Beijing National Laboratory For Molecular Sciences (BNLMS), Laboratory of New Materials, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China, and Graduate School of Chinese Academy of Sciences, Beijing 100049, China yanglm@iccas.ac.cn

J. Org. Chem., 2007, 72 (16), pp 6324–6327

DOI: 10.1021/jo0709448

Publication Date (Web): July 11, 2007

Section:

General Organic Chemistry

Abstract

trans-Haloarylbis(triphenylphosphine)nickel(II), a type of air- and moisture-stable Ni(II)−(σ-aryl) complex, was examined as catalyst precursor in the C−N coupling reaction. This type of Ni(II) pre-catalyst, associated with N-heterocyclic carbene ligands, is found to easily produce the catalytically active Ni(0) species in situ without the aid of external reductants and allows for the efficient amination of aryl chlorides with secondary cyclic amines and anilines under mild conditions.

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