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A Synthesis of Substituted α-Allenols via Iron-Catalyzed Cross-Coupling of Propargyl Carboxylates with Grignard Reagents
[Image: see text] α-Allenols are attractive and versatile compounds whose preparation can be a nontrivial task. In this Letter, we provide a method for the prompt synthesis of substituted α-allenols via a catalytic cross-coupling reaction which makes use of a nontoxic and cost-effective iron catalys...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American
Chemical Society
2016
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5100686/ https://www.ncbi.nlm.nih.gov/pubmed/27840771 http://dx.doi.org/10.1021/acscatal.6b02114 |
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author | Kessler, Simon N. Hundemer, Fabian Bäckvall, Jan-E. |
author_facet | Kessler, Simon N. Hundemer, Fabian Bäckvall, Jan-E. |
author_sort | Kessler, Simon N. |
collection | PubMed |
description | [Image: see text] α-Allenols are attractive and versatile compounds whose preparation can be a nontrivial task. In this Letter, we provide a method for the prompt synthesis of substituted α-allenols via a catalytic cross-coupling reaction which makes use of a nontoxic and cost-effective iron catalyst. The catalyst loading is typically as low as 1–5 mol %. The mild reaction conditions (−20 °C) and the short reaction time (15 min) allow for the presence of a variety of functional groups. Moreover, the reaction was shown to be scalable up to gram-scale and the propargyl substrates are readily accessible by a one-pot synthesis. |
format | Online Article Text |
id | pubmed-5100686 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | American
Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-51006862016-11-09 A Synthesis of Substituted α-Allenols via Iron-Catalyzed Cross-Coupling of Propargyl Carboxylates with Grignard Reagents Kessler, Simon N. Hundemer, Fabian Bäckvall, Jan-E. ACS Catal [Image: see text] α-Allenols are attractive and versatile compounds whose preparation can be a nontrivial task. In this Letter, we provide a method for the prompt synthesis of substituted α-allenols via a catalytic cross-coupling reaction which makes use of a nontoxic and cost-effective iron catalyst. The catalyst loading is typically as low as 1–5 mol %. The mild reaction conditions (−20 °C) and the short reaction time (15 min) allow for the presence of a variety of functional groups. Moreover, the reaction was shown to be scalable up to gram-scale and the propargyl substrates are readily accessible by a one-pot synthesis. American Chemical Society 2016-09-28 2016-11-04 /pmc/articles/PMC5100686/ /pubmed/27840771 http://dx.doi.org/10.1021/acscatal.6b02114 Text en Copyright © 2016 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Kessler, Simon N. Hundemer, Fabian Bäckvall, Jan-E. A Synthesis of Substituted α-Allenols via Iron-Catalyzed Cross-Coupling of Propargyl Carboxylates with Grignard Reagents |
title | A Synthesis of Substituted α-Allenols
via Iron-Catalyzed Cross-Coupling of Propargyl Carboxylates with Grignard
Reagents |
title_full | A Synthesis of Substituted α-Allenols
via Iron-Catalyzed Cross-Coupling of Propargyl Carboxylates with Grignard
Reagents |
title_fullStr | A Synthesis of Substituted α-Allenols
via Iron-Catalyzed Cross-Coupling of Propargyl Carboxylates with Grignard
Reagents |
title_full_unstemmed | A Synthesis of Substituted α-Allenols
via Iron-Catalyzed Cross-Coupling of Propargyl Carboxylates with Grignard
Reagents |
title_short | A Synthesis of Substituted α-Allenols
via Iron-Catalyzed Cross-Coupling of Propargyl Carboxylates with Grignard
Reagents |
title_sort | synthesis of substituted α-allenols
via iron-catalyzed cross-coupling of propargyl carboxylates with grignard
reagents |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5100686/ https://www.ncbi.nlm.nih.gov/pubmed/27840771 http://dx.doi.org/10.1021/acscatal.6b02114 |
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