Palladium(II)‐Catalysed Aminocarbonylation of Terminal Alkynes for the Synthesis of 2‐Ynamides: Addressing the Challenges of Solvents and Gas Mixtures

2‐Ynamides can be synthesised through Pd(II) catalysed oxidative carbonylation, utilising low catalyst loadings. A variety of alkynes and amines can be used to afford 2‐ynamides in high yields, whilst overcoming the drawbacks associated with previous oxidative methods, which rely on dangerous solven...

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Autores principales: Hughes, N. Louise, Brown, Clare L., Irwin, Andrew A., Cao, Qun, Muldoon, Mark J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5347853/
https://www.ncbi.nlm.nih.gov/pubmed/27906507
http://dx.doi.org/10.1002/cssc.201601601
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author Hughes, N. Louise
Brown, Clare L.
Irwin, Andrew A.
Cao, Qun
Muldoon, Mark J.
author_facet Hughes, N. Louise
Brown, Clare L.
Irwin, Andrew A.
Cao, Qun
Muldoon, Mark J.
author_sort Hughes, N. Louise
collection PubMed
description 2‐Ynamides can be synthesised through Pd(II) catalysed oxidative carbonylation, utilising low catalyst loadings. A variety of alkynes and amines can be used to afford 2‐ynamides in high yields, whilst overcoming the drawbacks associated with previous oxidative methods, which rely on dangerous solvents and gas mixtures. The use of [NBu(4)]I allows the utilisation of the industrially recommended solvent ethyl acetate. O(2) can be used as the terminal oxidant, and the catalyst can operate under safer conditions with low O(2) concentrations.
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spelling pubmed-53478532017-03-23 Palladium(II)‐Catalysed Aminocarbonylation of Terminal Alkynes for the Synthesis of 2‐Ynamides: Addressing the Challenges of Solvents and Gas Mixtures Hughes, N. Louise Brown, Clare L. Irwin, Andrew A. Cao, Qun Muldoon, Mark J. ChemSusChem Communications 2‐Ynamides can be synthesised through Pd(II) catalysed oxidative carbonylation, utilising low catalyst loadings. A variety of alkynes and amines can be used to afford 2‐ynamides in high yields, whilst overcoming the drawbacks associated with previous oxidative methods, which rely on dangerous solvents and gas mixtures. The use of [NBu(4)]I allows the utilisation of the industrially recommended solvent ethyl acetate. O(2) can be used as the terminal oxidant, and the catalyst can operate under safer conditions with low O(2) concentrations. John Wiley and Sons Inc. 2017-01-23 2017-02-22 /pmc/articles/PMC5347853/ /pubmed/27906507 http://dx.doi.org/10.1002/cssc.201601601 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Hughes, N. Louise
Brown, Clare L.
Irwin, Andrew A.
Cao, Qun
Muldoon, Mark J.
Palladium(II)‐Catalysed Aminocarbonylation of Terminal Alkynes for the Synthesis of 2‐Ynamides: Addressing the Challenges of Solvents and Gas Mixtures
title Palladium(II)‐Catalysed Aminocarbonylation of Terminal Alkynes for the Synthesis of 2‐Ynamides: Addressing the Challenges of Solvents and Gas Mixtures
title_full Palladium(II)‐Catalysed Aminocarbonylation of Terminal Alkynes for the Synthesis of 2‐Ynamides: Addressing the Challenges of Solvents and Gas Mixtures
title_fullStr Palladium(II)‐Catalysed Aminocarbonylation of Terminal Alkynes for the Synthesis of 2‐Ynamides: Addressing the Challenges of Solvents and Gas Mixtures
title_full_unstemmed Palladium(II)‐Catalysed Aminocarbonylation of Terminal Alkynes for the Synthesis of 2‐Ynamides: Addressing the Challenges of Solvents and Gas Mixtures
title_short Palladium(II)‐Catalysed Aminocarbonylation of Terminal Alkynes for the Synthesis of 2‐Ynamides: Addressing the Challenges of Solvents and Gas Mixtures
title_sort palladium(ii)‐catalysed aminocarbonylation of terminal alkynes for the synthesis of 2‐ynamides: addressing the challenges of solvents and gas mixtures
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5347853/
https://www.ncbi.nlm.nih.gov/pubmed/27906507
http://dx.doi.org/10.1002/cssc.201601601
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