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[Pt(PPh(3))(4)]-Catalyzed Selective Diboration of Symmetrical and Unsymmetrical 1,3-Diynes
[Image: see text] A straightforward, efficient, and selective method for the preparation of novel boryl-functionalized enynes or dienes via [Pt(PPh(3))(4)]-catalyzed diboration of a broad spectrum of symmetrical and unsymmetrical 1,3-diynes was developed. The catalytic cycle of diboration was propos...
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/PMC9396666/ https://www.ncbi.nlm.nih.gov/pubmed/35917577 http://dx.doi.org/10.1021/acs.joc.2c00844 |
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author | Szyling, Jakub Szymańska, Aleksandra Franczyk, Adrian Walkowiak, Jędrzej |
author_facet | Szyling, Jakub Szymańska, Aleksandra Franczyk, Adrian Walkowiak, Jędrzej |
author_sort | Szyling, Jakub |
collection | PubMed |
description | [Image: see text] A straightforward, efficient, and selective method for the preparation of novel boryl-functionalized enynes or dienes via [Pt(PPh(3))(4)]-catalyzed diboration of a broad spectrum of symmetrical and unsymmetrical 1,3-diynes was developed. The catalytic cycle of diboration was proposed on the basis of low-temperature (31)P NMR studies. An alternative isolation method via product condensation on a cold finger was developed, which, in contrast to previous literature reports, eliminates the need for the additional transformation of rapidly decomposing enynyl pinacol boronates to more stable silica-based column chromatography derivatives during the separation step. To prove the efficiency of this simple catalytic protocol, bisboryl-functionalized enynes were synthesized in a gram scale and tested as useful building blocks in advanced organic transformations, such as hydrosilylation and Suzuki and sila-Sonogashira couplings. The presence of silyl, boryl, as well as other functions like halogen or alkoxy in their structures builds a new class of multifunctionalized enynes that might be modified in various chemical reactions. |
format | Online Article Text |
id | pubmed-9396666 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-93966662022-08-24 [Pt(PPh(3))(4)]-Catalyzed Selective Diboration of Symmetrical and Unsymmetrical 1,3-Diynes Szyling, Jakub Szymańska, Aleksandra Franczyk, Adrian Walkowiak, Jędrzej J Org Chem [Image: see text] A straightforward, efficient, and selective method for the preparation of novel boryl-functionalized enynes or dienes via [Pt(PPh(3))(4)]-catalyzed diboration of a broad spectrum of symmetrical and unsymmetrical 1,3-diynes was developed. The catalytic cycle of diboration was proposed on the basis of low-temperature (31)P NMR studies. An alternative isolation method via product condensation on a cold finger was developed, which, in contrast to previous literature reports, eliminates the need for the additional transformation of rapidly decomposing enynyl pinacol boronates to more stable silica-based column chromatography derivatives during the separation step. To prove the efficiency of this simple catalytic protocol, bisboryl-functionalized enynes were synthesized in a gram scale and tested as useful building blocks in advanced organic transformations, such as hydrosilylation and Suzuki and sila-Sonogashira couplings. The presence of silyl, boryl, as well as other functions like halogen or alkoxy in their structures builds a new class of multifunctionalized enynes that might be modified in various chemical reactions. American Chemical Society 2022-08-02 2022-08-19 /pmc/articles/PMC9396666/ /pubmed/35917577 http://dx.doi.org/10.1021/acs.joc.2c00844 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 | Szyling, Jakub Szymańska, Aleksandra Franczyk, Adrian Walkowiak, Jędrzej [Pt(PPh(3))(4)]-Catalyzed Selective Diboration of Symmetrical and Unsymmetrical 1,3-Diynes |
title | [Pt(PPh(3))(4)]-Catalyzed
Selective Diboration of Symmetrical and Unsymmetrical 1,3-Diynes |
title_full | [Pt(PPh(3))(4)]-Catalyzed
Selective Diboration of Symmetrical and Unsymmetrical 1,3-Diynes |
title_fullStr | [Pt(PPh(3))(4)]-Catalyzed
Selective Diboration of Symmetrical and Unsymmetrical 1,3-Diynes |
title_full_unstemmed | [Pt(PPh(3))(4)]-Catalyzed
Selective Diboration of Symmetrical and Unsymmetrical 1,3-Diynes |
title_short | [Pt(PPh(3))(4)]-Catalyzed
Selective Diboration of Symmetrical and Unsymmetrical 1,3-Diynes |
title_sort | [pt(pph(3))(4)]-catalyzed
selective diboration of symmetrical and unsymmetrical 1,3-diynes |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9396666/ https://www.ncbi.nlm.nih.gov/pubmed/35917577 http://dx.doi.org/10.1021/acs.joc.2c00844 |
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