Interaction of benzene-1,2-diamines with isocyanide complexes of palladium(II): Insight into the mechanism

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Abstract

© 2016 Elsevier B.V. Reactivity of 4-toluidine (2) and 4,5-dimethylbenzene-1,2-diamine (3) were compared in coupling with the palladium-bis(isocyanide) complex cis-[PdCl2(CNXyl)2] (Xyl=2,6-Me2C6H3, 1), mixed isocyanide/diaminocarbene species cis-[PdCl2(CNXyl)(C(NHXyl)NH(4-C6H4CH3))] (4), and cis-[PdCl(CNXyl)(C(NHXyl)NHC6H2(Me)2 NH2)]Cl (5). In these Pd(II)-mediated reactions, 4,5-dimethylbenzene-1,2-diamine (3) was significantly more reactive than 4-toluidine (2), leading to the first mixed bis(diaminocarbene) complex cis-[PdCl(C(NHR)NHC6H2X2 NH2)(C(NHXyl)NH(4-C6H4CH3))]Cl (6) containing two different diaminocarbene ligands. Complex 6 was isolated and characterized by elemental analyses (C, H, N), HRESI+-MS, IR, 1H and 13C(1H) NMR spectroscopies, and single-crystal X-ray diffraction.
Original languageEnglish
Pages (from-to)607-612
JournalInorganica Chimica Acta
Volume455
DOIs
Publication statusPublished - 2017
Externally publishedYes

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Diamines
Palladium
Cyanides
diamines
Benzene
Nuclear magnetic resonance spectroscopy
palladium
Ligands
benzene
Single crystals
X ray diffraction
reactivity
interactions
nuclear magnetic resonance
ligands
single crystals
diffraction
spectroscopy
x rays
palladium chloride

Cite this

@article{c773e025d18e4310bfae0a611ce11a7a,
title = "Interaction of benzene-1,2-diamines with isocyanide complexes of palladium(II): Insight into the mechanism",
abstract = "{\circledC} 2016 Elsevier B.V. Reactivity of 4-toluidine (2) and 4,5-dimethylbenzene-1,2-diamine (3) were compared in coupling with the palladium-bis(isocyanide) complex cis-[PdCl2(CNXyl)2] (Xyl=2,6-Me2C6H3, 1), mixed isocyanide/diaminocarbene species cis-[PdCl2(CNXyl)(C(NHXyl)NH(4-C6H4CH3))] (4), and cis-[PdCl(CNXyl)(C(NHXyl)NHC6H2(Me)2 NH2)]Cl (5). In these Pd(II)-mediated reactions, 4,5-dimethylbenzene-1,2-diamine (3) was significantly more reactive than 4-toluidine (2), leading to the first mixed bis(diaminocarbene) complex cis-[PdCl(C(NHR)NHC6H2X2 NH2)(C(NHXyl)NH(4-C6H4CH3))]Cl (6) containing two different diaminocarbene ligands. Complex 6 was isolated and characterized by elemental analyses (C, H, N), HRESI+-MS, IR, 1H and 13C(1H) NMR spectroscopies, and single-crystal X-ray diffraction.",
author = "M.A. Kinzhalov and G.L. Starova and V.P. Boyarskiy",
year = "2017",
doi = "10.1016/j.ica.2016.05.014",
language = "English",
volume = "455",
pages = "607--612",
journal = "Inorganica Chimica Acta",
issn = "0020-1693",
publisher = "Elsevier",

}

TY - JOUR

T1 - Interaction of benzene-1,2-diamines with isocyanide complexes of palladium(II): Insight into the mechanism

AU - Kinzhalov, M.A.

AU - Starova, G.L.

AU - Boyarskiy, V.P.

PY - 2017

Y1 - 2017

N2 - © 2016 Elsevier B.V. Reactivity of 4-toluidine (2) and 4,5-dimethylbenzene-1,2-diamine (3) were compared in coupling with the palladium-bis(isocyanide) complex cis-[PdCl2(CNXyl)2] (Xyl=2,6-Me2C6H3, 1), mixed isocyanide/diaminocarbene species cis-[PdCl2(CNXyl)(C(NHXyl)NH(4-C6H4CH3))] (4), and cis-[PdCl(CNXyl)(C(NHXyl)NHC6H2(Me)2 NH2)]Cl (5). In these Pd(II)-mediated reactions, 4,5-dimethylbenzene-1,2-diamine (3) was significantly more reactive than 4-toluidine (2), leading to the first mixed bis(diaminocarbene) complex cis-[PdCl(C(NHR)NHC6H2X2 NH2)(C(NHXyl)NH(4-C6H4CH3))]Cl (6) containing two different diaminocarbene ligands. Complex 6 was isolated and characterized by elemental analyses (C, H, N), HRESI+-MS, IR, 1H and 13C(1H) NMR spectroscopies, and single-crystal X-ray diffraction.

AB - © 2016 Elsevier B.V. Reactivity of 4-toluidine (2) and 4,5-dimethylbenzene-1,2-diamine (3) were compared in coupling with the palladium-bis(isocyanide) complex cis-[PdCl2(CNXyl)2] (Xyl=2,6-Me2C6H3, 1), mixed isocyanide/diaminocarbene species cis-[PdCl2(CNXyl)(C(NHXyl)NH(4-C6H4CH3))] (4), and cis-[PdCl(CNXyl)(C(NHXyl)NHC6H2(Me)2 NH2)]Cl (5). In these Pd(II)-mediated reactions, 4,5-dimethylbenzene-1,2-diamine (3) was significantly more reactive than 4-toluidine (2), leading to the first mixed bis(diaminocarbene) complex cis-[PdCl(C(NHR)NHC6H2X2 NH2)(C(NHXyl)NH(4-C6H4CH3))]Cl (6) containing two different diaminocarbene ligands. Complex 6 was isolated and characterized by elemental analyses (C, H, N), HRESI+-MS, IR, 1H and 13C(1H) NMR spectroscopies, and single-crystal X-ray diffraction.

U2 - 10.1016/j.ica.2016.05.014

DO - 10.1016/j.ica.2016.05.014

M3 - Article

VL - 455

SP - 607

EP - 612

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

SN - 0020-1693

ER -