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Pyridine wingtip in ▫$[Pd(Py-tzNHC)_2]^{2+}$▫ complex is a proton shuttle in the catalytic hydroamination of alkynes
Virant, Miha (Author), Mihelač, Mateja (Author), Gazvoda, Martin (Author), Cotman, Andrej Emanuel (Author), Frantar, Anja (Author), Pinter, Balazs (Author), Košmrlj, Janez (Author)

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Abstract
The cationic palladium(II) complex 1 of pyridylmesoionic 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.

Language:English
Keywords:catalysis, palladium, hydroamination, metal-ligand cooperation, proton transfer, DFT, hydrocarbons, chemical reactions, reaction mechanisms, metals, pyridines
Work type:Article (dk_c)
Tipology:1.01 - Original Scientific Article
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2020
Number of pages:Str. 2157-2161
Numbering:Vol. 22, iss. 6
UDC:547.82:546.98
ISSN on article:1523-7060
DOI:10.1021/acs.orglett.0c00203 This link opens in a new window
COBISS.SI-ID:1538522051 This link opens in a new window
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Downloads:108
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Record is a part of a journal

Title:Organic letters
Shortened title:Org. lett.
Publisher:American Chemical Society
ISSN:1523-7060
COBISS.SI-ID:1916442 This link opens in a new window

Document is financed by a project

Funder:ARRS - Agencija za raziskovalno dejavnost Republike Slovenije (ARRS)
Project no.:P1-0230
Name:Organska kemija: sinteza, struktura in aplikacija

Funder:ARRS - Agencija za raziskovalno dejavnost Republike Slovenije (ARRS)
Project no.:J1-8147
Name:Ligandi s tzNHC strukturo v organokovinski kemiji in homogeni katalizi: tvorba vezi C-C in C-N v vodi

Funder:ARRS - Agencija za raziskovalno dejavnost Republike Slovenije (ARRS)
Project no.:J1-9166
Name:Redefinicija in razširitev uporabe Sonogashirove reakcije pripajanja brez bakra

Funder:ARRS - Agencija za raziskovalno dejavnost Republike Slovenije (ARRS)
Funding Programme:Young Researcher Grant

Funder:Drugi - Drug financer ali več financerjev
Funding Programme:Ministry of Education, Science and Sport, Republic of Slovenia
Name:PhD Scholarship

Funder:Drugi - Drug financer ali več financerjev
Funding Programme:Universidad Técnico Federico Santa Maria, Department of Chemistry

Licences

License:CC BY 4.0, Creative Commons Attribution 4.0 International
Link:http://creativecommons.org/licenses/by/4.0/
Description:This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.
Licensing start date:12.03.2021

Secondary language

Language:Slovenian
Keywords:kataliza, paladij, hidroaminiranje, sodelovanje kovina-ligand, prenos protona, DFT, hidrokarbonati, kemijske reakcije, mehanizmi reakcij, kovine, piridini

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