Cu-catalyzed, Mn-mediated propargylation and allenylation of aldehydes with propargyl bromides

A simple, practical, and high chemo-selective method for the synthesis of propargyl alcohol and allenyl alcohols via Cu-catalyzed, Mn-mediated propargylation and allenylation of aldehydes with propargyl bromides has been established. When 3-bromo-1-propyne was conducted under the standard condition,...

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Autores principales: Zhang, Rongli, Xia, Yanping, Yan, Yuchen, Ouyang, Lu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer International Publishing 2022
Materias:
Research Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8933908/
https://www.ncbi.nlm.nih.gov/pubmed/35303949
http://dx.doi.org/10.1186/s13065-022-00803-3
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author Zhang, Rongli
Xia, Yanping
Yan, Yuchen
Ouyang, Lu
author_facet Zhang, Rongli
Xia, Yanping
Yan, Yuchen
Ouyang, Lu
author_sort Zhang, Rongli
collection PubMed
description A simple, practical, and high chemo-selective method for the synthesis of propargyl alcohol and allenyl alcohols via Cu-catalyzed, Mn-mediated propargylation and allenylation of aldehydes with propargyl bromides has been established. When 3-bromo-1-propyne was conducted under the standard condition, the aldehydes were transformed to the corresponding propargylation products completely, while when 1-bromo-2-pentyne was used, allenic alcohol was the only product. Variety of homopropargyl alcohols and allenyl alcohols were obtained in high yields and the reaction is compatible with broad substrate scopes. In addition, the large-scale reaction could also be proceeded smoothly indicating the potential synthetic applications of this transformation. GRAPHICAL ABSTRACT: [Image: see text] SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1186/s13065-022-00803-3.
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spelling pubmed-89339082022-03-23 Cu-catalyzed, Mn-mediated propargylation and allenylation of aldehydes with propargyl bromides Zhang, Rongli Xia, Yanping Yan, Yuchen Ouyang, Lu BMC Chem Research Article A simple, practical, and high chemo-selective method for the synthesis of propargyl alcohol and allenyl alcohols via Cu-catalyzed, Mn-mediated propargylation and allenylation of aldehydes with propargyl bromides has been established. When 3-bromo-1-propyne was conducted under the standard condition, the aldehydes were transformed to the corresponding propargylation products completely, while when 1-bromo-2-pentyne was used, allenic alcohol was the only product. Variety of homopropargyl alcohols and allenyl alcohols were obtained in high yields and the reaction is compatible with broad substrate scopes. In addition, the large-scale reaction could also be proceeded smoothly indicating the potential synthetic applications of this transformation. GRAPHICAL ABSTRACT: [Image: see text] SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1186/s13065-022-00803-3. Springer International Publishing 2022-03-18 /pmc/articles/PMC8933908/ /pubmed/35303949 http://dx.doi.org/10.1186/s13065-022-00803-3 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/ (https://creativecommons.org/publicdomain/zero/1.0/) ) applies to the data made available in this article, unless otherwise stated in a credit line to the data.
spellingShingle Research Article
Zhang, Rongli
Xia, Yanping
Yan, Yuchen
Ouyang, Lu
Cu-catalyzed, Mn-mediated propargylation and allenylation of aldehydes with propargyl bromides
title Cu-catalyzed, Mn-mediated propargylation and allenylation of aldehydes with propargyl bromides
title_full Cu-catalyzed, Mn-mediated propargylation and allenylation of aldehydes with propargyl bromides
title_fullStr Cu-catalyzed, Mn-mediated propargylation and allenylation of aldehydes with propargyl bromides
title_full_unstemmed Cu-catalyzed, Mn-mediated propargylation and allenylation of aldehydes with propargyl bromides
title_short Cu-catalyzed, Mn-mediated propargylation and allenylation of aldehydes with propargyl bromides
title_sort cu-catalyzed, mn-mediated propargylation and allenylation of aldehydes with propargyl bromides
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8933908/
https://www.ncbi.nlm.nih.gov/pubmed/35303949
http://dx.doi.org/10.1186/s13065-022-00803-3
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AT yanyuchen cucatalyzedmnmediatedpropargylationandallenylationofaldehydeswithpropargylbromides
AT ouyanglu cucatalyzedmnmediatedpropargylationandallenylationofaldehydeswithpropargylbromides

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