Pyridine Wingtip in [Pd(Py-tzNHC)2]2+ Complex Is a Proton Shuttle in the Catalytic Hydroamination of Alkynes
Miha Virant
1, 2
,
Mateja Mihelač
1
,
Martin Gazvoda
1
,
Andrej Emanuel Cotman
1
,
Anja Frantar
1
,
Balazs Pinter
2
,
Janez Kosmrlj
1
2
Departamento de Quı́mica, Universidad Técnica Federico Santa Marı́a, Av. España 1680, 2390123 Valparaı́so, Chile
|
Publication type: Journal Article
Publication date: 2020-01-30
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
31999464
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
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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Virant M. et al. Pyridine Wingtip in [Pd(Py-tzNHC)2]2+ Complex Is a Proton Shuttle in the Catalytic Hydroamination of Alkynes // Organic Letters. 2020. Vol. 22. No. 6. pp. 2157-2161.
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Virant M., Mihelač M., Gazvoda M., Cotman A. E., Frantar A., Pinter B., Kosmrlj J. Pyridine Wingtip in [Pd(Py-tzNHC)2]2+ Complex Is a Proton Shuttle in the Catalytic Hydroamination of Alkynes // Organic Letters. 2020. Vol. 22. No. 6. pp. 2157-2161.
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RIS
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TY - JOUR
DO - 10.1021/acs.orglett.0c00203
UR - https://doi.org/10.1021/acs.orglett.0c00203
TI - Pyridine Wingtip in [Pd(Py-tzNHC)2]2+ Complex Is a Proton Shuttle in the Catalytic Hydroamination of Alkynes
T2 - Organic Letters
AU - Virant, Miha
AU - Mihelač, Mateja
AU - Gazvoda, Martin
AU - Cotman, Andrej Emanuel
AU - Frantar, Anja
AU - Pinter, Balazs
AU - Kosmrlj, Janez
PY - 2020
DA - 2020/01/30
PB - American Chemical Society (ACS)
SP - 2157-2161
IS - 6
VL - 22
PMID - 31999464
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2020_Virant,
author = {Miha Virant and Mateja Mihelač and Martin Gazvoda and Andrej Emanuel Cotman and Anja Frantar and Balazs Pinter and Janez Kosmrlj},
title = {Pyridine Wingtip in [Pd(Py-tzNHC)2]2+ Complex Is a Proton Shuttle in the Catalytic Hydroamination of Alkynes},
journal = {Organic Letters},
year = {2020},
volume = {22},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/acs.orglett.0c00203},
number = {6},
pages = {2157--2161},
doi = {10.1021/acs.orglett.0c00203}
}
Cite this
MLA
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Virant, Miha, et al. “Pyridine Wingtip in [Pd(Py-tzNHC)2]2+ Complex Is a Proton Shuttle in the Catalytic Hydroamination of Alkynes.” Organic Letters, vol. 22, no. 6, Jan. 2020, pp. 2157-2161. https://doi.org/10.1021/acs.orglett.0c00203.