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
Hauptverfasser: 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
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container_end_page 7473
container_issue 35
container_start_page 7468
container_title Organic letters
container_volume 26
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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title Base-Mediated Allylic Defluorinative Functionalizations of β‑CF2H‑1,3-enynes Enables the Construction of Terminal Monofluoroenynes
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