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Synthesis 2010(24): 4235-4241  
DOI: 10.1055/s-0030-1258281
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Direct Oxidative Conversion of Alcohols, Aldehydes and Amines into Nitriles Using Hypervalent Iodine(III) Reagent

Chenjie Zhu, Chengguo Sun, 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 18 August 2010
Publication Date:
30 September 2010 (online)

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Abstract

An efficient, facile, and high-yielding procedure for the direct oxidative conversion of alcohols, aldehydes, and primary, secondary, and tertiary amines into the corresponding nitriles using the hypervalent iodine(III) reagent hydroxy(tosyloxy)iodobenzene in combination with ammonium acetate as a nitrogen source is reported. The oxidation proceeded in mixed solvent to afford nitriles in excellent yields and high selectivity even at room temperature. Selective oxidation of primary amines in the presence of secondary amines and tertiary amines was also achieved. A possible mechanism for the oxidation is proposed.

Key words

alcohols - aldehydes - amines - hypervalent iodine - oxidations