Please use this identifier to cite or link to this item:
http://hdl.handle.net/10397/90733
DC Field | Value | Language |
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dc.contributor | Department of Applied Biology and Chemical Technology | - |
dc.creator | Du, B | - |
dc.creator | Chan, CM | - |
dc.creator | Lee, PY | - |
dc.creator | Cheung, LH | - |
dc.creator | Xu, X | - |
dc.creator | Lin, Z | - |
dc.creator | Yu, WY | - |
dc.date.accessioned | 2021-09-03T02:33:23Z | - |
dc.date.available | 2021-09-03T02:33:23Z | - |
dc.identifier.uri | http://hdl.handle.net/10397/90733 | - |
dc.language.iso | en | en_US |
dc.publisher | Nature Publishing Group | en_US |
dc.rights | © The Author(s) 2021 | en_US |
dc.rights | This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/. | en_US |
dc.rights | The following publication Du, B., Chan, CM., Lee, PY. et al. 2,2-difluorovinyl benzoates for diverse synthesis of gem-difluoroenol ethers by Ni-catalyzed cross-coupling reactions. Nat Commun 12(1), 412 (2021) is available at https://doi.org/10.1038/s41467-020-20725-9 | en_US |
dc.title | 2,2-difluorovinyl benzoates for diverse synthesis of gem-difluoroenol ethers by Ni-catalyzed cross-coupling reactions | en_US |
dc.type | Journal/Magazine Article | en_US |
dc.identifier.volume | 12 | - |
dc.identifier.issue | 1 | - |
dc.identifier.doi | 10.1038/s41467-020-20725-9 | - |
dcterms.abstract | gem-Difluoroalkene is a bioisostere of carbonyl group for improving bioavailability of drug candidates. Herein we develop structurally diverse 2,2-difluorovinyl benzoates (BzO-DFs) as versatile building blocks for modular synthesis of gem-difluoroenol ethers (44 examples) and gem-difluoroalkenes (2 examples) by Ni-catalyzed cross coupling reactions. Diverse BzO-DFs derivatives bearing sensitive functional groups (e.g., C = C, TMS, strained carbocycles) are readily prepared from their bromodifluoroacetates and bromodifluoroketones precursors using metallic zinc as reductant. With Ni(COD)2 and dppf [1,1’-bis(diphenylphosphino)ferrocene] as catalyst, reactions of BzO-DFs with arylboronic acids and arylmagnesium/alkylzinc reagents afforded the desired gem-difluoroenol ethers and gem-difluoroalkenes in good yields. The Ni-catalyzed coupling reactions features highly regioselective C(vinyl)–O(benzoate) bond activation of the BzO-DFs. Results from control experiments and DFT calculations are consistent with a mechanism involving initial oxidative addition of the BzO-DFs by the Ni(0) complex. By virtue of diversity of the BzO-DFs and excellent functional group tolerance, this method is amenable to late-stage functionalization of multifunctionalized bioactive molecules. | - |
dcterms.accessRights | open access | en_US |
dcterms.bibliographicCitation | Nature communications, 2021, v. 12, no. 1, 412 | - |
dcterms.isPartOf | Nature communications | - |
dcterms.issued | 2021 | - |
dc.identifier.scopus | 2-s2.0-85100129101 | - |
dc.identifier.pmid | 33462244 | - |
dc.identifier.eissn | 2041-1723 | - |
dc.identifier.artn | 412 | - |
dc.description.validate | 202109 bcvc | - |
dc.description.oa | Version of Record | en_US |
dc.identifier.FolderNumber | OA_Scopus/WOS | en_US |
dc.description.pubStatus | Published | en_US |
Appears in Collections: | Journal/Magazine Article |
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File | Description | Size | Format | |
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s41467-020-20725-9.pdf | 1.05 MB | Adobe PDF | View/Open |
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