Site‐Selective (Z)‐α‐Borylalkenyl Copper Systems for Nucleophilic Stereodefined Allylic Coupling

1,1‐Diborylalkenes can be transformed into (Z)‐skipped dienes through Cu(I)‐phosphine catalyzed allylic coupling reactions. The energetically preferred formation of (Z)‐α‐borylalkenyl copper (I) species and the subsequent nucleophilic attack, explains the stereoselective nucleophilic substitution wi...

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Autores principales: Pujol, Mireia, Maza, Ricardo J., Salvado, Oriol, Carbó, Jorge J., Fernández, Elena
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9540588/
https://www.ncbi.nlm.nih.gov/pubmed/35857816
http://dx.doi.org/10.1002/anie.202208495
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author Pujol, Mireia
Maza, Ricardo J.
Salvado, Oriol
Carbó, Jorge J.
Fernández, Elena
author_facet Pujol, Mireia
Maza, Ricardo J.
Salvado, Oriol
Carbó, Jorge J.
Fernández, Elena
author_sort Pujol, Mireia
collection PubMed
description 1,1‐Diborylalkenes can be transformed into (Z)‐skipped dienes through Cu(I)‐phosphine catalyzed allylic coupling reactions. The energetically preferred formation of (Z)‐α‐borylalkenyl copper (I) species and the subsequent nucleophilic attack, explains the stereoselective nucleophilic substitution with allyl bromides. The eventual treatment of (Z)‐skipped dienes with NaO( t )Bu promotes cyclization/aromatization patterns via enyne intermediates.
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spelling pubmed-95405882022-10-14 Site‐Selective (Z)‐α‐Borylalkenyl Copper Systems for Nucleophilic Stereodefined Allylic Coupling Pujol, Mireia Maza, Ricardo J. Salvado, Oriol Carbó, Jorge J. Fernández, Elena Angew Chem Int Ed Engl Communications 1,1‐Diborylalkenes can be transformed into (Z)‐skipped dienes through Cu(I)‐phosphine catalyzed allylic coupling reactions. The energetically preferred formation of (Z)‐α‐borylalkenyl copper (I) species and the subsequent nucleophilic attack, explains the stereoselective nucleophilic substitution with allyl bromides. The eventual treatment of (Z)‐skipped dienes with NaO( t )Bu promotes cyclization/aromatization patterns via enyne intermediates. John Wiley and Sons Inc. 2022-08-08 2022-09-12 /pmc/articles/PMC9540588/ /pubmed/35857816 http://dx.doi.org/10.1002/anie.202208495 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ (https://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Pujol, Mireia
Maza, Ricardo J.
Salvado, Oriol
Carbó, Jorge J.
Fernández, Elena
Site‐Selective (Z)‐α‐Borylalkenyl Copper Systems for Nucleophilic Stereodefined Allylic Coupling
title Site‐Selective (Z)‐α‐Borylalkenyl Copper Systems for Nucleophilic Stereodefined Allylic Coupling
title_full Site‐Selective (Z)‐α‐Borylalkenyl Copper Systems for Nucleophilic Stereodefined Allylic Coupling
title_fullStr Site‐Selective (Z)‐α‐Borylalkenyl Copper Systems for Nucleophilic Stereodefined Allylic Coupling
title_full_unstemmed Site‐Selective (Z)‐α‐Borylalkenyl Copper Systems for Nucleophilic Stereodefined Allylic Coupling
title_short Site‐Selective (Z)‐α‐Borylalkenyl Copper Systems for Nucleophilic Stereodefined Allylic Coupling
title_sort site‐selective (z)‐α‐borylalkenyl copper systems for nucleophilic stereodefined allylic coupling
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9540588/
https://www.ncbi.nlm.nih.gov/pubmed/35857816
http://dx.doi.org/10.1002/anie.202208495
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