Pd-Catalyzed Hydroamination of Alkoxyallenes with Azole Heterocycles: Examples and Mechanistic Proposal

[Image: see text] Palladium-catalyzed regio- and enantioselective addition of azole heterocycles to alkoxyallenes was developed (up to 92% yields and up to 94% ee). DFT calculations suggest a new Pd(0)-driven mechanistic pathway proceeding through protonation of the Pd-coordinated allene (4-PdL(2)),...

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Autores principales: Bernar, Ivan, Fiser, Béla, Blanco-Ania, Daniel, Gómez-Bengoa, Enrique, Rutjes, Floris P. J. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5565904/
https://www.ncbi.nlm.nih.gov/pubmed/28786679
http://dx.doi.org/10.1021/acs.orglett.7b01826
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author Bernar, Ivan
Fiser, Béla
Blanco-Ania, Daniel
Gómez-Bengoa, Enrique
Rutjes, Floris P. J. T.
author_facet Bernar, Ivan
Fiser, Béla
Blanco-Ania, Daniel
Gómez-Bengoa, Enrique
Rutjes, Floris P. J. T.
author_sort Bernar, Ivan
collection PubMed
description [Image: see text] Palladium-catalyzed regio- and enantioselective addition of azole heterocycles to alkoxyallenes was developed (up to 92% yields and up to 94% ee). DFT calculations suggest a new Pd(0)-driven mechanistic pathway proceeding through protonation of the Pd-coordinated allene (4-PdL(2)), which develops a strongly nucleophilic character at the central C atom.
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spelling pubmed-55659042017-08-23 Pd-Catalyzed Hydroamination of Alkoxyallenes with Azole Heterocycles: Examples and Mechanistic Proposal Bernar, Ivan Fiser, Béla Blanco-Ania, Daniel Gómez-Bengoa, Enrique Rutjes, Floris P. J. T. Org Lett [Image: see text] Palladium-catalyzed regio- and enantioselective addition of azole heterocycles to alkoxyallenes was developed (up to 92% yields and up to 94% ee). DFT calculations suggest a new Pd(0)-driven mechanistic pathway proceeding through protonation of the Pd-coordinated allene (4-PdL(2)), which develops a strongly nucleophilic character at the central C atom. American Chemical Society 2017-08-08 2017-08-18 /pmc/articles/PMC5565904/ /pubmed/28786679 http://dx.doi.org/10.1021/acs.orglett.7b01826 Text en Copyright © 2017 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Bernar, Ivan
Fiser, Béla
Blanco-Ania, Daniel
Gómez-Bengoa, Enrique
Rutjes, Floris P. J. T.
Pd-Catalyzed Hydroamination of Alkoxyallenes with Azole Heterocycles: Examples and Mechanistic Proposal
title Pd-Catalyzed Hydroamination of Alkoxyallenes with Azole Heterocycles: Examples and Mechanistic Proposal
title_full Pd-Catalyzed Hydroamination of Alkoxyallenes with Azole Heterocycles: Examples and Mechanistic Proposal
title_fullStr Pd-Catalyzed Hydroamination of Alkoxyallenes with Azole Heterocycles: Examples and Mechanistic Proposal
title_full_unstemmed Pd-Catalyzed Hydroamination of Alkoxyallenes with Azole Heterocycles: Examples and Mechanistic Proposal
title_short Pd-Catalyzed Hydroamination of Alkoxyallenes with Azole Heterocycles: Examples and Mechanistic Proposal
title_sort pd-catalyzed hydroamination of alkoxyallenes with azole heterocycles: examples and mechanistic proposal
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5565904/
https://www.ncbi.nlm.nih.gov/pubmed/28786679
http://dx.doi.org/10.1021/acs.orglett.7b01826
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