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Highly Stereoselective and One-Pot Synthesis of Tetra-substituted Monofluoroalkenes with Aldehydes and Fluorobis(phenylsulfonyl)methane

Highly Stereoselective and One-Pot Synthesis of Tetra-substituted Monofluoroalkenes with Aldehydes and Fluorobis(phenylsulfonyl)methane
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摘要 A highly stereoselective synthesis of tetrasubstituted monofluoroalkenes with aldehydes and fluorobis(phenyl- sulfonyl)methane (FBSM) in one pot has been developed. The reaction was amenable topara- and meta-substituted aryl aldehydes, 2-naphthaldehyde, and cinnamaldehyde, giving phenylsulfonyl-substituted monofluoroalkenes in 40%--86% yields with 98/2- 99/1 Z/E ratios. The presence of the sulfonyl group enables the further transformation of the products into more useful monofluoroalkenes. A highly stereoselective synthesis of tetrasubstituted monofluoroalkenes with aldehydes and fluorobis(phenyl- sulfonyl)methane (FBSM) in one pot has been developed. The reaction was amenable topara- and meta-substituted aryl aldehydes, 2-naphthaldehyde, and cinnamaldehyde, giving phenylsulfonyl-substituted monofluoroalkenes in 40%--86% yields with 98/2- 99/1 Z/E ratios. The presence of the sulfonyl group enables the further transformation of the products into more useful monofluoroalkenes.
出处 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2013年第7期878-884,共7页 中国化学(英文版)
基金 Acknowledgement Support of our work by the National Natural Science Foundation of China (Nos. 20825209 and 21202189), the National Basic Research Program of China (Nos. 2012CB215500 and 2012CB821600), the Chinese Academy of Sciences, and the Syngenta PhD Studentship (to X.S.) is gratefully acknowledged.
关键词 OLEFINATION ALDEHYDES nucleophilic addition SULFONES FLUORINE olefination, aldehydes, nucleophilic addition, sulfones, fluorine
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