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Copper(I)-Catalyzed Regio- and Stereoselective Silaboration of Terminal Allenes
[Image: see text] Organic compounds bearing both silyl and boryl groups are important building blocks in organic synthesis because of the adequate reactivity of the silyl and boryl groups and high stereospecificity in their derivatization reactions. The difference in reactivity between the silyl and...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10080722/ https://www.ncbi.nlm.nih.gov/pubmed/37035279 http://dx.doi.org/10.1021/acsorginorgau.2c00057 |
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author | Ozawa, Yu Koriyama, Hisao Shiratori, Yuma Ito, Hajime |
author_facet | Ozawa, Yu Koriyama, Hisao Shiratori, Yuma Ito, Hajime |
author_sort | Ozawa, Yu |
collection | PubMed |
description | [Image: see text] Organic compounds bearing both silyl and boryl groups are important building blocks in organic synthesis because of the adequate reactivity of the silyl and boryl groups and high stereospecificity in their derivatization reactions. The difference in reactivity between the silyl and boryl groups enables stepwise derivatization of these groups to afford complex molecules. Here, we report the copper(I)-catalyzed silaboration of terminal allenes to produce multisubstituted allylic boronates embedded with an alkenyl silane structure. The reaction can proceed with a variety of allenes and silylboranes. Furthermore, the silyl and boryl groups were successfully converted into other functional groups, while retaining the stereochemistry of the alkene moiety. |
format | Online Article Text |
id | pubmed-10080722 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-100807222023-04-08 Copper(I)-Catalyzed Regio- and Stereoselective Silaboration of Terminal Allenes Ozawa, Yu Koriyama, Hisao Shiratori, Yuma Ito, Hajime ACS Org Inorg Au [Image: see text] Organic compounds bearing both silyl and boryl groups are important building blocks in organic synthesis because of the adequate reactivity of the silyl and boryl groups and high stereospecificity in their derivatization reactions. The difference in reactivity between the silyl and boryl groups enables stepwise derivatization of these groups to afford complex molecules. Here, we report the copper(I)-catalyzed silaboration of terminal allenes to produce multisubstituted allylic boronates embedded with an alkenyl silane structure. The reaction can proceed with a variety of allenes and silylboranes. Furthermore, the silyl and boryl groups were successfully converted into other functional groups, while retaining the stereochemistry of the alkene moiety. American Chemical Society 2023-01-04 /pmc/articles/PMC10080722/ /pubmed/37035279 http://dx.doi.org/10.1021/acsorginorgau.2c00057 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Ozawa, Yu Koriyama, Hisao Shiratori, Yuma Ito, Hajime Copper(I)-Catalyzed Regio- and Stereoselective Silaboration of Terminal Allenes |
title | Copper(I)-Catalyzed
Regio- and Stereoselective Silaboration
of Terminal Allenes |
title_full | Copper(I)-Catalyzed
Regio- and Stereoselective Silaboration
of Terminal Allenes |
title_fullStr | Copper(I)-Catalyzed
Regio- and Stereoselective Silaboration
of Terminal Allenes |
title_full_unstemmed | Copper(I)-Catalyzed
Regio- and Stereoselective Silaboration
of Terminal Allenes |
title_short | Copper(I)-Catalyzed
Regio- and Stereoselective Silaboration
of Terminal Allenes |
title_sort | copper(i)-catalyzed
regio- and stereoselective silaboration
of terminal allenes |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10080722/ https://www.ncbi.nlm.nih.gov/pubmed/37035279 http://dx.doi.org/10.1021/acsorginorgau.2c00057 |
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