Pyridine Wingtip in [Pd(Py-tzNHC)(2)](2+) Complex Is a Proton Shuttle in the Catalytic Hydroamination of Alkynes

[Image: see text] The cationic palladium(II) complex 1 of pyridyl-mesoionic carbene ligand catalyzes Markovnikov-selective intermolecular hydroamination between anilines and terminal alkynes into the corresponding imines. The reaction proceeds at room temperature, in the absence of additives, with e...

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Autores principales: Virant, Miha, Mihelač, Mateja, Gazvoda, Martin, Cotman, Andrej E., Frantar, Anja, Pinter, Balazs, Košmrlj, Janez
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7308070/
https://www.ncbi.nlm.nih.gov/pubmed/31999464
http://dx.doi.org/10.1021/acs.orglett.0c00203
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author Virant, Miha
Mihelač, Mateja
Gazvoda, Martin
Cotman, Andrej E.
Frantar, Anja
Pinter, Balazs
Košmrlj, Janez
author_facet Virant, Miha
Mihelač, Mateja
Gazvoda, Martin
Cotman, Andrej E.
Frantar, Anja
Pinter, Balazs
Košmrlj, Janez
author_sort Virant, Miha
collection PubMed
description [Image: see text] The cationic palladium(II) complex 1 of pyridyl-mesoionic carbene ligand catalyzes Markovnikov-selective intermolecular hydroamination between anilines and terminal alkynes into the corresponding imines. The reaction proceeds at room temperature, in the absence of additives, with exquisite selectivity and diverse functional group tolerance. The key intrinsic feature of the catalyst is the pyridine wingtip confined to the proximity of the alkynophilic metal active site, which mimics the function of enzyme-like architectures by assisting entropically favored proton transfers.
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spelling pubmed-73080702020-06-23 Pyridine Wingtip in [Pd(Py-tzNHC)(2)](2+) Complex Is a Proton Shuttle in the Catalytic Hydroamination of Alkynes Virant, Miha Mihelač, Mateja Gazvoda, Martin Cotman, Andrej E. Frantar, Anja Pinter, Balazs Košmrlj, Janez Org Lett [Image: see text] The cationic palladium(II) complex 1 of pyridyl-mesoionic carbene ligand catalyzes Markovnikov-selective intermolecular hydroamination between anilines and terminal alkynes into the corresponding imines. The reaction proceeds at room temperature, in the absence of additives, with exquisite selectivity and diverse functional group tolerance. The key intrinsic feature of the catalyst is the pyridine wingtip confined to the proximity of the alkynophilic metal active site, which mimics the function of enzyme-like architectures by assisting entropically favored proton transfers. American Chemical Society 2020-01-30 2020-03-20 /pmc/articles/PMC7308070/ /pubmed/31999464 http://dx.doi.org/10.1021/acs.orglett.0c00203 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Virant, Miha
Mihelač, Mateja
Gazvoda, Martin
Cotman, Andrej E.
Frantar, Anja
Pinter, Balazs
Košmrlj, Janez
Pyridine Wingtip in [Pd(Py-tzNHC)(2)](2+) Complex Is a Proton Shuttle in the Catalytic Hydroamination of Alkynes
title Pyridine Wingtip in [Pd(Py-tzNHC)(2)](2+) Complex Is a Proton Shuttle in the Catalytic Hydroamination of Alkynes
title_full Pyridine Wingtip in [Pd(Py-tzNHC)(2)](2+) Complex Is a Proton Shuttle in the Catalytic Hydroamination of Alkynes
title_fullStr Pyridine Wingtip in [Pd(Py-tzNHC)(2)](2+) Complex Is a Proton Shuttle in the Catalytic Hydroamination of Alkynes
title_full_unstemmed Pyridine Wingtip in [Pd(Py-tzNHC)(2)](2+) Complex Is a Proton Shuttle in the Catalytic Hydroamination of Alkynes
title_short Pyridine Wingtip in [Pd(Py-tzNHC)(2)](2+) Complex Is a Proton Shuttle in the Catalytic Hydroamination of Alkynes
title_sort pyridine wingtip in [pd(py-tznhc)(2)](2+) complex is a proton shuttle in the catalytic hydroamination of alkynes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7308070/
https://www.ncbi.nlm.nih.gov/pubmed/31999464
http://dx.doi.org/10.1021/acs.orglett.0c00203
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