Base-Mediated Allylic Defluorinative Functionalizations of β‑CF2H‑1,3-enynes Enables the Construction of Terminal Monofluoroenynes

The base-mediated allylic defluorinative functionalization of β-CF2H-1,3-enynes with nucleophiles is described, affording terminal monofluoroalkenes bearing an alkynyl group in synthetically useful yields and Z/E selectivities. Importantly, the resultant Z/E mixture could be separated by flash chrom...

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Published inOrganic letters Vol. 26; no. 35; pp. 7468 - 7473
Main Authors He, Zhi-Qing, Chen, Shu-Jie, Chen, Guo-Shu, Dong, Bao-Le, Lin, Jin-Hao, Zhong, Yu, Wu, Jia-Ming, Ren, Zhi, Liu, Yun-Lin
Format Journal Article
LanguageEnglish
Published American Chemical Society 06.09.2024
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Summary:The base-mediated allylic defluorinative functionalization of β-CF2H-1,3-enynes with nucleophiles is described, affording terminal monofluoroalkenes bearing an alkynyl group in synthetically useful yields and Z/E selectivities. Importantly, the resultant Z/E mixture could be separated by flash chromatography in all cases; thus, stereoisomerically pure monofluoroenynes were obtained. Postsynthetic modifications of the synthesized monofluoroenynes were also accomplished to access diverse molecular structures. Computational studies disclosed the origin of the diastereoselectivity.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c02874