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Synthesis 2012; 44(21): 3315-3320
DOI: 10.1055/s-0032-1316799
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 5-(Trifluoromethyl)-2,5-dihydro-1,2λ5-oxaphospholes by a One-Pot Three-Component Reaction

Hua-Fang Fan
a   Shaanxi Engineering Center of Bioresource Chemistry and Sustainable Utilization, College of Science, Northwest A & F University, Yangling, Shaanxi 712100, P. R. of China
b   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)64166128   Email: zhusz@mail.sioc.ac.cn
,
Xiao-Wei Wang
b   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)64166128   Email: zhusz@mail.sioc.ac.cn
,
Jing-Wei Zhao
b   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)64166128   Email: zhusz@mail.sioc.ac.cn
,
Xin-Jin Li
b   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)64166128   Email: zhusz@mail.sioc.ac.cn
,
Jin-Ming Gao*
a   Shaanxi Engineering Center of Bioresource Chemistry and Sustainable Utilization, College of Science, Northwest A & F University, Yangling, Shaanxi 712100, P. R. of China
,
Shi-Zheng Zhu*
b   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)64166128   Email: zhusz@mail.sioc.ac.cn
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Publication History

Received: 10 July 2012

Accepted after revision: 18 September 2012

Publication Date:
02 October 2012 (online)

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Abstract

A series of trifluoromethyl-substituted 1,2λ5-oxaphospholes were prepared in yields of up to 95% by a one-pot three-component­ reaction under mild conditions. The zwitterionic intermediate generated by attack of triphenylphosphine on an alkyl propiolate reacts with an aryl or styryl trifluoromethyl ketone to form the 1,2λ5-oxaphosphole ring. All the new products were characterized by IR, NMR, and mass spectroscopy and the structure of one of them, ethyl 2,2,2-triphenyl-5-[(E)-2-phenylvinyl]-5-(trifluoromethyl)-2,5-dihydro-1,2λ5-oxaphosphole-4-carboxylate, was confirmed by X-ray single-crystal diffraction analysis.

Key words

heterocycles - phosphorus - fluorine - oxaphospholes - alkynes - ketones

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