Selective Nucleophilic Oxygenation of Palladium-Bound Isocyanide Ligands: Route to Imine Complexes That Serve as Efficient Catalysts for Copper-/Phosphine-Free Sonogashira Reactions
2
Publication type: Journal Article
Publication date: 2013-03-06
scimago Q2
wos Q1
SJR: 0.676
CiteScore: 5.1
Impact factor: 2.9
ISSN: 02767333, 15206041
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
Metal-mediated reactions between cis-[PdCl2(CNR)2] (R = Xy (1), Cy (2), tBu (3), C6H3(Cl-2)Me-6 (4)) and the ketonitrones Ph2C═N(O)C6H4R′ (R′ = Me (5), Cl (6)) proceed in a 1:1 molar ratio as selective nucleophilic oxygenations and provide the imine–isocyanide complexes [PdCl2{N(C6H4R′)═CPh2}(CNR)] (7–14: R′ = Me, R = Xy (7), Cy (8), tBu (9), C6H3(Cl-2)Me-6 (10); R′ = Cl, R = Xy (11), Cy (12), tBu (13), C6H3(Cl-2)Me-6 (14)) in excellent yields (90–94%), while the reaction of the cis-[PdCl2(CNR)2] complexes with aldonitrones proceeds as 1,3-dipolar cycloaddition, giving carbene adducts which then convert to the imine complexes. Theoretical calculations at the DFT level indicate that, in the case of aldonitrones, formation of the imine complexes occurs preferably via a cycloaddition/splitting pathway, including the generation of a cycloadduct, while, in the case of ketonitrones, both the cycloaddition/splitting route and the direct oxygen atom transfer pathway are equally plausible from a kinetic viewpoint....
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Kritchenkov A. S. et al. Selective Nucleophilic Oxygenation of Palladium-Bound Isocyanide Ligands: Route to Imine Complexes That Serve as Efficient Catalysts for Copper-/Phosphine-Free Sonogashira Reactions // Organometallics. 2013. Vol. 32. No. 6. pp. 1979-1987.
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Kritchenkov A. S., Luzyanin K., Bokach N. A., Kuznetsov M., Gurzhiy V. V., Kukushkin V. Y. Selective Nucleophilic Oxygenation of Palladium-Bound Isocyanide Ligands: Route to Imine Complexes That Serve as Efficient Catalysts for Copper-/Phosphine-Free Sonogashira Reactions // Organometallics. 2013. Vol. 32. No. 6. pp. 1979-1987.
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RIS
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TY - JOUR
DO - 10.1021/om4000665
UR - https://doi.org/10.1021/om4000665
TI - Selective Nucleophilic Oxygenation of Palladium-Bound Isocyanide Ligands: Route to Imine Complexes That Serve as Efficient Catalysts for Copper-/Phosphine-Free Sonogashira Reactions
T2 - Organometallics
AU - Kritchenkov, Andreii S.
AU - Luzyanin, Konstantin
AU - Bokach, Nadezhda A.
AU - Kuznetsov, Maxim
AU - Gurzhiy, Vladislav V.
AU - Kukushkin, Vadim Yu.
PY - 2013
DA - 2013/03/06
PB - American Chemical Society (ACS)
SP - 1979-1987
IS - 6
VL - 32
SN - 0276-7333
SN - 1520-6041
ER -
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@article{2013_Kritchenkov,
author = {Andreii S. Kritchenkov and Konstantin Luzyanin and Nadezhda A. Bokach and Maxim Kuznetsov and Vladislav V. Gurzhiy and Vadim Yu. Kukushkin},
title = {Selective Nucleophilic Oxygenation of Palladium-Bound Isocyanide Ligands: Route to Imine Complexes That Serve as Efficient Catalysts for Copper-/Phosphine-Free Sonogashira Reactions},
journal = {Organometallics},
year = {2013},
volume = {32},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/om4000665},
number = {6},
pages = {1979--1987},
doi = {10.1021/om4000665}
}
Cite this
MLA
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Kritchenkov, Andreii S., et al. “Selective Nucleophilic Oxygenation of Palladium-Bound Isocyanide Ligands: Route to Imine Complexes That Serve as Efficient Catalysts for Copper-/Phosphine-Free Sonogashira Reactions.” Organometallics, vol. 32, no. 6, Mar. 2013, pp. 1979-1987. https://doi.org/10.1021/om4000665.
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