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Enantioselective Copper-Catalyzed sp(2)/sp(3) Diborylation of 1-Chloro-1-Trifluoromethylalkenes
[Image: see text] Fluorine-containing organoboron compounds have emerged as novel building blocks in chemical synthesis; among them, fluorinated sp(2)/sp(3) diborylated compounds are particularly appealing, since they might undergo chemoselective and diversified transformations of different C–B bond...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9413839/ https://www.ncbi.nlm.nih.gov/pubmed/36032759 http://dx.doi.org/10.1021/acscentsci.2c00339 |
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author | Fan, Zhenwei Ye, Mingxing Wang, Yahao Qiu, Jian Li, Wangyang Ma, Xingxing Yang, Kai Song, Qiuling |
author_facet | Fan, Zhenwei Ye, Mingxing Wang, Yahao Qiu, Jian Li, Wangyang Ma, Xingxing Yang, Kai Song, Qiuling |
author_sort | Fan, Zhenwei |
collection | PubMed |
description | [Image: see text] Fluorine-containing organoboron compounds have emerged as novel building blocks in chemical synthesis; among them, fluorinated sp(2)/sp(3) diborylated compounds are particularly appealing, since they might undergo chemoselective and diversified transformations of different C–B bonds with fluorinated functionality, thus bringing versatility and complexity to the eventual products. However, expedient, synthetic strategies for the construction of such fluorinated diborylative compounds are very sparse. Herein, we disclose enantioselective Cu-catalyzed sp(2)/sp(3) diborylations of 1-chloro-1-trifluoromethylalkenes, leading to diborylated compounds bearing a gem-difluoroalkenyl moiety; most intriguingly, the new formed C–B bonds include one stereoselective and optically pure Csp(3)–B bond. Further transformations on the eventual products demonstrated the values of our presented strategy. |
format | Online Article Text |
id | pubmed-9413839 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-94138392022-08-27 Enantioselective Copper-Catalyzed sp(2)/sp(3) Diborylation of 1-Chloro-1-Trifluoromethylalkenes Fan, Zhenwei Ye, Mingxing Wang, Yahao Qiu, Jian Li, Wangyang Ma, Xingxing Yang, Kai Song, Qiuling ACS Cent Sci [Image: see text] Fluorine-containing organoboron compounds have emerged as novel building blocks in chemical synthesis; among them, fluorinated sp(2)/sp(3) diborylated compounds are particularly appealing, since they might undergo chemoselective and diversified transformations of different C–B bonds with fluorinated functionality, thus bringing versatility and complexity to the eventual products. However, expedient, synthetic strategies for the construction of such fluorinated diborylative compounds are very sparse. Herein, we disclose enantioselective Cu-catalyzed sp(2)/sp(3) diborylations of 1-chloro-1-trifluoromethylalkenes, leading to diborylated compounds bearing a gem-difluoroalkenyl moiety; most intriguingly, the new formed C–B bonds include one stereoselective and optically pure Csp(3)–B bond. Further transformations on the eventual products demonstrated the values of our presented strategy. American Chemical Society 2022-07-20 2022-08-24 /pmc/articles/PMC9413839/ /pubmed/36032759 http://dx.doi.org/10.1021/acscentsci.2c00339 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Fan, Zhenwei Ye, Mingxing Wang, Yahao Qiu, Jian Li, Wangyang Ma, Xingxing Yang, Kai Song, Qiuling Enantioselective Copper-Catalyzed sp(2)/sp(3) Diborylation of 1-Chloro-1-Trifluoromethylalkenes |
title | Enantioselective
Copper-Catalyzed sp(2)/sp(3) Diborylation of 1-Chloro-1-Trifluoromethylalkenes |
title_full | Enantioselective
Copper-Catalyzed sp(2)/sp(3) Diborylation of 1-Chloro-1-Trifluoromethylalkenes |
title_fullStr | Enantioselective
Copper-Catalyzed sp(2)/sp(3) Diborylation of 1-Chloro-1-Trifluoromethylalkenes |
title_full_unstemmed | Enantioselective
Copper-Catalyzed sp(2)/sp(3) Diborylation of 1-Chloro-1-Trifluoromethylalkenes |
title_short | Enantioselective
Copper-Catalyzed sp(2)/sp(3) Diborylation of 1-Chloro-1-Trifluoromethylalkenes |
title_sort | enantioselective
copper-catalyzed sp(2)/sp(3) diborylation of 1-chloro-1-trifluoromethylalkenes |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9413839/ https://www.ncbi.nlm.nih.gov/pubmed/36032759 http://dx.doi.org/10.1021/acscentsci.2c00339 |
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