Oxidative Addition of Aryl Halides to a Triphosphine Ni(0) Center to Form Pentacoordinate Ni(II) Aryl Species

[Image: see text] Oxidative addition of aryl halides to Ni(0) is a ubiquitous elementary step in cross-coupling and related reactions, usually producing a square-planar Ni(II)–aryl intermediate. Here we show that a triphosphine ligand supports oxidative addition at a tris-ligated Ni(0) center to cle...

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Autores principales: Pérez−García, Pablo M., Darù, Andrea, Scheerder, Arthur R., Lutz, Martin, Harvey, Jeremy N., Moret, Marc-Etienne
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7189616/
https://www.ncbi.nlm.nih.gov/pubmed/32362705
http://dx.doi.org/10.1021/acs.organomet.0c00060
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author Pérez−García, Pablo M.
Darù, Andrea
Scheerder, Arthur R.
Lutz, Martin
Harvey, Jeremy N.
Moret, Marc-Etienne
author_facet Pérez−García, Pablo M.
Darù, Andrea
Scheerder, Arthur R.
Lutz, Martin
Harvey, Jeremy N.
Moret, Marc-Etienne
author_sort Pérez−García, Pablo M.
collection PubMed
description [Image: see text] Oxidative addition of aryl halides to Ni(0) is a ubiquitous elementary step in cross-coupling and related reactions, usually producing a square-planar Ni(II)–aryl intermediate. Here we show that a triphosphine ligand supports oxidative addition at a tris-ligated Ni(0) center to cleanly form stable five-coordinate Ni(II)–aryl compounds. Kinetic and computational studies support a concerted, two-electron mechanism rather than radical halogen abstraction. These results support the idea that oxidative addition to triphosphine Ni(0) species may be more generally involved in Ni/phosphine catalytic systems.
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spelling pubmed-71896162020-04-30 Oxidative Addition of Aryl Halides to a Triphosphine Ni(0) Center to Form Pentacoordinate Ni(II) Aryl Species Pérez−García, Pablo M. Darù, Andrea Scheerder, Arthur R. Lutz, Martin Harvey, Jeremy N. Moret, Marc-Etienne Organometallics [Image: see text] Oxidative addition of aryl halides to Ni(0) is a ubiquitous elementary step in cross-coupling and related reactions, usually producing a square-planar Ni(II)–aryl intermediate. Here we show that a triphosphine ligand supports oxidative addition at a tris-ligated Ni(0) center to cleanly form stable five-coordinate Ni(II)–aryl compounds. Kinetic and computational studies support a concerted, two-electron mechanism rather than radical halogen abstraction. These results support the idea that oxidative addition to triphosphine Ni(0) species may be more generally involved in Ni/phosphine catalytic systems. American Chemical Society 2020-04-03 2020-04-27 /pmc/articles/PMC7189616/ /pubmed/32362705 http://dx.doi.org/10.1021/acs.organomet.0c00060 Text en Copyright © 2020 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 Pérez−García, Pablo M.
Darù, Andrea
Scheerder, Arthur R.
Lutz, Martin
Harvey, Jeremy N.
Moret, Marc-Etienne
Oxidative Addition of Aryl Halides to a Triphosphine Ni(0) Center to Form Pentacoordinate Ni(II) Aryl Species
title Oxidative Addition of Aryl Halides to a Triphosphine Ni(0) Center to Form Pentacoordinate Ni(II) Aryl Species
title_full Oxidative Addition of Aryl Halides to a Triphosphine Ni(0) Center to Form Pentacoordinate Ni(II) Aryl Species
title_fullStr Oxidative Addition of Aryl Halides to a Triphosphine Ni(0) Center to Form Pentacoordinate Ni(II) Aryl Species
title_full_unstemmed Oxidative Addition of Aryl Halides to a Triphosphine Ni(0) Center to Form Pentacoordinate Ni(II) Aryl Species
title_short Oxidative Addition of Aryl Halides to a Triphosphine Ni(0) Center to Form Pentacoordinate Ni(II) Aryl Species
title_sort oxidative addition of aryl halides to a triphosphine ni(0) center to form pentacoordinate ni(ii) aryl species
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7189616/
https://www.ncbi.nlm.nih.gov/pubmed/32362705
http://dx.doi.org/10.1021/acs.organomet.0c00060
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