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Pd-catalyzed sp–sp(3) cross-coupling of benzyl bromides using lithium acetylides
Organolithium-based cross-coupling reactions have emerged as an indispensable method to construct C–C bonds. These transformations have proven particularly useful for the direct and fast coupling of various organolithium reagents (sp, sp(2), and sp(3)) with aromatic (pseudo) halides (sp(2)). Here we...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8320736/ https://www.ncbi.nlm.nih.gov/pubmed/34236070 http://dx.doi.org/10.1039/d1cc02762j |
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author | Mondal, Anirban Visser, Paco Doze, Anna M. Buter, Jeffrey Feringa, Ben L. |
author_facet | Mondal, Anirban Visser, Paco Doze, Anna M. Buter, Jeffrey Feringa, Ben L. |
author_sort | Mondal, Anirban |
collection | PubMed |
description | Organolithium-based cross-coupling reactions have emerged as an indispensable method to construct C–C bonds. These transformations have proven particularly useful for the direct and fast coupling of various organolithium reagents (sp, sp(2), and sp(3)) with aromatic (pseudo) halides (sp(2)). Here we present an efficient method for the cross-coupling of benzyl bromides (sp(3)) with lithium acetylides (sp). The reaction proceeds within 10 min at room temperature and can be performed in the presence of organolithium-sensitive functional groups such as esters, nitriles, amides and boronic esters. The potential application of the methodology is demonstrated in the preparation of key intermediates used in pharmaceuticals, chemical biology and natural products. |
format | Online Article Text |
id | pubmed-8320736 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-83207362021-08-09 Pd-catalyzed sp–sp(3) cross-coupling of benzyl bromides using lithium acetylides Mondal, Anirban Visser, Paco Doze, Anna M. Buter, Jeffrey Feringa, Ben L. Chem Commun (Camb) Chemistry Organolithium-based cross-coupling reactions have emerged as an indispensable method to construct C–C bonds. These transformations have proven particularly useful for the direct and fast coupling of various organolithium reagents (sp, sp(2), and sp(3)) with aromatic (pseudo) halides (sp(2)). Here we present an efficient method for the cross-coupling of benzyl bromides (sp(3)) with lithium acetylides (sp). The reaction proceeds within 10 min at room temperature and can be performed in the presence of organolithium-sensitive functional groups such as esters, nitriles, amides and boronic esters. The potential application of the methodology is demonstrated in the preparation of key intermediates used in pharmaceuticals, chemical biology and natural products. The Royal Society of Chemistry 2021-07-01 /pmc/articles/PMC8320736/ /pubmed/34236070 http://dx.doi.org/10.1039/d1cc02762j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Mondal, Anirban Visser, Paco Doze, Anna M. Buter, Jeffrey Feringa, Ben L. Pd-catalyzed sp–sp(3) cross-coupling of benzyl bromides using lithium acetylides |
title | Pd-catalyzed sp–sp(3) cross-coupling of benzyl bromides using lithium acetylides |
title_full | Pd-catalyzed sp–sp(3) cross-coupling of benzyl bromides using lithium acetylides |
title_fullStr | Pd-catalyzed sp–sp(3) cross-coupling of benzyl bromides using lithium acetylides |
title_full_unstemmed | Pd-catalyzed sp–sp(3) cross-coupling of benzyl bromides using lithium acetylides |
title_short | Pd-catalyzed sp–sp(3) cross-coupling of benzyl bromides using lithium acetylides |
title_sort | pd-catalyzed sp–sp(3) cross-coupling of benzyl bromides using lithium acetylides |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8320736/ https://www.ncbi.nlm.nih.gov/pubmed/34236070 http://dx.doi.org/10.1039/d1cc02762j |
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