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Synthesis 2014; 46(03): 320-330
DOI: 10.1055/s-0033-1340317
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© Georg Thieme Verlag Stuttgart · New York

One-Pot Transition-Metal-Free Synthesis of Weinreb Amides Directly from Carboxylic Acids

Teng Niu
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Anning Road 967 (E), Lanzhou 730070, P. R. of China   Fax: +86(931)7971989   Email: huangdf@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
,
Ke-Hu Wang
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Anning Road 967 (E), Lanzhou 730070, P. R. of China   Fax: +86(931)7971989   Email: huangdf@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
,
Danfeng Huang*
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Anning Road 967 (E), Lanzhou 730070, P. R. of China   Fax: +86(931)7971989   Email: huangdf@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
,
Changming Xu
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Anning Road 967 (E), Lanzhou 730070, P. R. of China   Fax: +86(931)7971989   Email: huangdf@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
,
Yingpeng Su
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Anning Road 967 (E), Lanzhou 730070, P. R. of China   Fax: +86(931)7971989   Email: huangdf@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
,
Yulai Hu*
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Anning Road 967 (E), Lanzhou 730070, P. R. of China   Fax: +86(931)7971989   Email: huangdf@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
b   State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
,
Ying Fu
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Anning Road 967 (E), Lanzhou 730070, P. R. of China   Fax: +86(931)7971989   Email: huangdf@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
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Publication History

Received: 16 September 2013

Accepted after revision: 08 November 2013

Publication Date:
12 December 2013 (online)

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Abstract

Weinreb amides were prepared directly from carboxylic acids, N,O-dimethylhydroxylamine, and phosphorus trichloride in one pot at 60 °C in toluene in high yields, thus avoiding the separation of the moisture and air sensitive intermediate P[NMe(OMe)]3 in advance. Sterically hindered carboxylic acids also give the corresponding Weinreb amides in excellent yields. Various functional groups are tolerated on the carboxylic acid. The method, which is a simple process and gives high yields, is suitable for large-scale production.

Key words

Weinreb amides - carboxylic acids - one-pot reaction - coupling - synthesis

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