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Synthesis 2016; 48(05): 751-760
DOI: 10.1055/s-0035-1561298
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Allenylphosphonates through Cu(I)-Catalyzed Coupling­ of Terminal Alkynes with Diazophosphonates

Chenggui Wu
a   College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, P. R. of China   Email: gsdeng@hunnu.edu.cn
b   Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China   Email: wangjb@pku.edu.cn
,
Fei Ye
b   Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China   Email: wangjb@pku.edu.cn
,
Guojiao Wu
b   Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China   Email: wangjb@pku.edu.cn
,
Shuai Xu
b   Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China   Email: wangjb@pku.edu.cn
,
Guisheng Deng*
a   College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, P. R. of China   Email: gsdeng@hunnu.edu.cn
,
Yan Zhang
b   Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China   Email: wangjb@pku.edu.cn
,
Jianbo Wang*
b   Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China   Email: wangjb@pku.edu.cn
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Publication History

Received: 15 October 2015

Accepted after revision: 26 November 2015

Publication Date:
04 January 2016 (online)

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Abstract

Through the Cu(I)-catalyzed coupling of diazophosphonates with terminal alkynes, an efficient method for the synthesis of allenylphosphonates has been developed. Simple and inexpensive CuI is used as the catalyst and the reaction is conducted under mild conditions.

Key words

diazophosphonate - allene - cross-coupling - carbene - copper

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561298.
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