Palladium(II)-Mediated Addition of Benzenediamines to Isocyanides: Generation of Three Types of Diaminocarbene Ligands Depending on the Isomeric Structure of the Nucleophile
M. A. Kinzhalov
1
,
Svetlana A Timofeeva
1
,
Konstantin Luzyanin
1, 2
,
Anton A Yakimanskiy
1
,
Matti Haukka
3
,
Publication type: Journal Article
Publication date: 2016-01-13
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
Coupling of the palladium-bis(isocyanide) complexes cis-[PdCl2(CNR)2] (R = 2,6-Me2C6H3 1, 2-Cl-6-MeC6H3 2) with benzene-1,3-diamine (BDA1) leads to the diaminocarbene species cis-[PdCl2(CNR){C(NHR)═NH(1,3-C6H4NH2)}] (5 and 6, respectively). In this reaction, BDA1 behaves as a monofunctional nucleophile that adds to one of the RNC ligands by one amino group. By contrast, the reaction of 1 and 2 with benzene-1,4-diamine (BDA2) involves both amino functionalities of the diamine and leads to the binuclear species [cis-PdCl2(CNR){μ-C(NHR)═NH(1,4-C6H4)NH═C(NHR)}-(cis)-PdCl2(CNR)] (6 and 7) featuring two 1,4-bifunctional diaminocarbene ligands. The reaction of cis-[PdCl2(CNR)2] (R = cyclohexyl 3) with either BDA1 or BDA2 does not afford any isolable carbene derivatives. The most versatile chemistry was observed when 1–3 were treated with benzene-1,2-diamine (BDA3) and the relevant substituted 1,2-diamines, viz., 4,5-dimethylbenzene-1,2-diamine (BDA4) and 4,5-dichlorobenzene-1,2-diamine (BDA5). The addition of th...
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Kinzhalov M. A. et al. Palladium(II)-Mediated Addition of Benzenediamines to Isocyanides: Generation of Three Types of Diaminocarbene Ligands Depending on the Isomeric Structure of the Nucleophile // Organometallics. 2016. Vol. 35. No. 2. pp. 218-228.
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Kinzhalov M. A., Timofeeva S. A., Luzyanin K., Boyarskiy V. P., Yakimanskiy A. A., Haukka M., Kukushkin V. Y. Palladium(II)-Mediated Addition of Benzenediamines to Isocyanides: Generation of Three Types of Diaminocarbene Ligands Depending on the Isomeric Structure of the Nucleophile // Organometallics. 2016. Vol. 35. No. 2. pp. 218-228.
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TY - JOUR
DO - 10.1021/acs.organomet.5b00936
UR - https://doi.org/10.1021/acs.organomet.5b00936
TI - Palladium(II)-Mediated Addition of Benzenediamines to Isocyanides: Generation of Three Types of Diaminocarbene Ligands Depending on the Isomeric Structure of the Nucleophile
T2 - Organometallics
AU - Kinzhalov, M. A.
AU - Timofeeva, Svetlana A
AU - Luzyanin, Konstantin
AU - Boyarskiy, Vadim P
AU - Yakimanskiy, Anton A
AU - Haukka, Matti
AU - Kukushkin, Vadim Yu.
PY - 2016
DA - 2016/01/13
PB - American Chemical Society (ACS)
SP - 218-228
IS - 2
VL - 35
SN - 0276-7333
SN - 1520-6041
ER -
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@article{2016_Kinzhalov,
author = {M. A. Kinzhalov and Svetlana A Timofeeva and Konstantin Luzyanin and Vadim P Boyarskiy and Anton A Yakimanskiy and Matti Haukka and Vadim Yu. Kukushkin},
title = {Palladium(II)-Mediated Addition of Benzenediamines to Isocyanides: Generation of Three Types of Diaminocarbene Ligands Depending on the Isomeric Structure of the Nucleophile},
journal = {Organometallics},
year = {2016},
volume = {35},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/acs.organomet.5b00936},
number = {2},
pages = {218--228},
doi = {10.1021/acs.organomet.5b00936}
}
Cite this
MLA
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Kinzhalov, M. A., et al. “Palladium(II)-Mediated Addition of Benzenediamines to Isocyanides: Generation of Three Types of Diaminocarbene Ligands Depending on the Isomeric Structure of the Nucleophile.” Organometallics, vol. 35, no. 2, Jan. 2016, pp. 218-228. https://doi.org/10.1021/acs.organomet.5b00936.
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