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Pyridine wingtip in ▫$[Pd(Py-tzNHC)_2]^{2+}$▫ complex is a proton shuttle in the catalytic hydroamination of alkynes
ID
Virant, Miha
(
Author
),
ID
Mihelač, Mateja
(
Author
),
ID
Gazvoda, Martin
(
Author
),
ID
Cotman, Andrej Emanuel
(
Author
),
ID
Frantar, Anja
(
Author
),
ID
Pinter, Balazs
(
Author
),
ID
Košmrlj, Janez
(
Author
)
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MD5: 929D5DEA8B35D00FDA7B695116819BB9
URL - Source URL, Visit
https://pubs.acs.org/doi/10.1021/acs.orglett.0c00203
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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
Typology:
1.01 - Original Scientific Article
Organization:
FKKT - Faculty of Chemistry and Chemical Technology
Publication status:
Published
Publication version:
Version of Record
Year:
2020
Number of pages:
Str. 2157-2161
Numbering:
Vol. 22, iss. 6
PID:
20.500.12556/RUL-125377
UDC:
547.82:546.98
ISSN on article:
1523-7060
DOI:
10.1021/acs.orglett.0c00203
COBISS.SI-ID:
1538522051
Publication date in RUL:
12.03.2021
Views:
1126
Downloads:
274
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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
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
Projects
Funder:
ARRS - Slovenian Research Agency
Project number:
P1-0230
Name:
Organska kemija: sinteza, struktura in aplikacija
Funder:
ARRS - Slovenian Research Agency
Project number:
J1-8147
Name:
Ligandi s tzNHC strukturo v organokovinski kemiji in homogeni katalizi: tvorba vezi C-C in C-N v vodi
Funder:
ARRS - Slovenian Research Agency
Project number:
J1-9166
Name:
Redefinicija in razširitev uporabe Sonogashirove reakcije pripajanja brez bakra
Funder:
ARRS - Slovenian Research Agency
Funding programme:
Young Researcher Grant
Funder:
Other - Other funder or multiple funders
Funding programme:
Ministry of Education, Science and Sport, Republic of Slovenia
Name:
PhD Scholarship
Funder:
Other - Other funder or multiple funders
Funding programme:
Universidad Técnico Federico Santa Maria, Department of Chemistry
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