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Synlett 2011(8): 1174-1178  
DOI: 10.1055/s-0030-1260531
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Iron-Catalyzed Nitrene Insertion Reaction for Facile Construction of Amide Compounds

Guo-Qiang Chena, Zhen-Jiang Xua, Yungen Liub, Cong-Ying Zhoub, Chi-Ming Che*a,b
a Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, 345 Lingling Road, Shanghai, P. R. of China
b State Key Laboratory on Synthetic Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. of China
Fax: +85228571586; e-Mail: cmche@hku.hk;
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Publication History

Received 14 January 2011
Publication Date:
20 April 2011 (online)

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Abstract

A facile method for the construction of amide compounds from aldehydes by an iron-catalyzed nitrene insertion reaction has been developed. Both aryl and aliphatic aldehydes can directly afford the corresponding amides with an iron(II)-terpyridine (tpy) complex formed in situ as catalyst, and PhI=NTs as nitrogen source under mild reaction conditions. An ESI-MS study revealed the formation of [Fe(tpy)2(NTs)]²+ as a reaction intermediate.

Key words

nitrene - C-H insertion - iron - catalysis - amide