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Synthesis 2010(18): 3121-3125  
DOI: 10.1055/s-0030-1258162
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Facile and Efficient One-Pot Synthesis of Nitriles from Aldehydes Using Hypervalent Iodine(III) Reagents in Aqueous Ammonium Acetate

Chenjie Zhu, Lei Ji, Yunyang Wei*
School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China
Fax: +86(25)84317078; e-Mail: ywei@mail.njust.edu.cn;
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Publication History

Received 8 April 2010
Publication Date:
07 July 2010 (online)

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Abstract

A facile procedure for the direct oxidation of aldehydes to the corresponding nitriles using either the hypervalent iodine(III) reagent PhI(OAc)2 or a polymer-supported hypervalent iodine(III) reagent poly{4-[bis(acetoxy)iodo]}styrene as oxidant is reported. The oxidation proceeded in water at 70 ˚C in the presence of sodium dodecylsulfate using ammonium acetate as nitrogen source. The reaction was complete in four hours for the oxidation of benzylic and allylic aldehydes, and gave more than 90% yield in most cases. For the oxidation of aliphatic aldehydes, moderate to excellent yields of nitriles were also obtained after prolonged reaction times.

Key words

aldehydes - hypervalent iodine - nitriles - oxidations - polymers