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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Veröffentlicht in: | Organic letters 2024-09, Vol.26 (35), p.7468-7473 |
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creator | 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 |
description | 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. |
doi_str_mv | 10.1021/acs.orglett.4c02874 |
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Lett</addtitle><date>2024-09-06</date><risdate>2024</risdate><volume>26</volume><issue>35</issue><spage>7468</spage><epage>7473</epage><pages>7468-7473</pages><issn>1523-7060</issn><issn>1523-7052</issn><eissn>1523-7052</eissn><abstract>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. 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title | Base-Mediated Allylic Defluorinative Functionalizations of β‑CF2H‑1,3-enynes Enables the Construction of Terminal Monofluoroenynes |
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