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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...

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Autores principales: Ozawa, Yu, Koriyama, Hisao, Shiratori, Yuma, Ito, Hajime
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
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.
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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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