Synthesis, Characterization, and Reactivity of N-Heterocyclic Carbene Palladium(II) Hydroxide Dimers

Jonathan D. Egbert; Anthony Chartoire; Alexandra M. Z. Slawin; Steven P. Nolan

doi:10.1021/om200579h

Synthesis, Characterization, and Reactivity of N-Heterocyclic Carbene Palladium(II) Hydroxide Dimers

Jonathan D. Egbert, Anthony Chartoire, Alexandra M. Z. Slawin, Steven P. Nolan

Research output: Contribution to journal › Article › peer-review

Abstract

Palladium hydroxide dimers were prepared by reactions of CsOH with monomeric [Pd(NHC)(eta(3)-allyl)Cl] starting materials. The dimers represent species proposed as intermediates in important cross-coupling reactions. These complexes were tested for their catalytic activity in Suzuki-Miyaura coupling and Buchwald-Hartwig aryl amination. The hydroxide complexes were susceptible to hydrogenolysis on exposure to H-2 gas. Following H2O elimination and beta-hydride elimination of an additional cinnamyl ligand, a Pd(0) species is formed which can react with other available ligands.

Original language	English
Pages (from-to)	4494-4496
Number of pages	3
Journal	Organometallics
Volume	30
Issue number	17
DOIs	https://doi.org/10.1021/om200579h
Publication status	Published - 12 Sept 2011

Keywords

CROSS-COUPLING REACTIONS
PINCER COMPLEXES
BUCHWALD-HARTWIG
SUZUKI-MIYAURA
BONDS
HYDROGENATION
MONONUCLEAR
HCL

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title = "Synthesis, Characterization, and Reactivity of N-Heterocyclic Carbene Palladium(II) Hydroxide Dimers",

abstract = "Palladium hydroxide dimers were prepared by reactions of CsOH with monomeric [Pd(NHC)(eta(3)-allyl)Cl] starting materials. The dimers represent species proposed as intermediates in important cross-coupling reactions. These complexes were tested for their catalytic activity in Suzuki-Miyaura coupling and Buchwald-Hartwig aryl amination. The hydroxide complexes were susceptible to hydrogenolysis on exposure to H-2 gas. Following H2O elimination and beta-hydride elimination of an additional cinnamyl ligand, a Pd(0) species is formed which can react with other available ligands.",

keywords = "CROSS-COUPLING REACTIONS, PINCER COMPLEXES, BUCHWALD-HARTWIG, SUZUKI-MIYAURA, BONDS, HYDROGENATION, MONONUCLEAR, HCL",

author = "Egbert, {Jonathan D.} and Anthony Chartoire and Slawin, {Alexandra M. Z.} and Nolan, {Steven P.}",

year = "2011",

month = sep,

day = "12",

doi = "10.1021/om200579h",

language = "English",

volume = "30",

pages = "4494--4496",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society (ACS)",

number = "17",

}

TY - JOUR

T1 - Synthesis, Characterization, and Reactivity of N-Heterocyclic Carbene Palladium(II) Hydroxide Dimers

AU - Egbert, Jonathan D.

AU - Chartoire, Anthony

AU - Slawin, Alexandra M. Z.

AU - Nolan, Steven P.

PY - 2011/9/12

Y1 - 2011/9/12

N2 - Palladium hydroxide dimers were prepared by reactions of CsOH with monomeric [Pd(NHC)(eta(3)-allyl)Cl] starting materials. The dimers represent species proposed as intermediates in important cross-coupling reactions. These complexes were tested for their catalytic activity in Suzuki-Miyaura coupling and Buchwald-Hartwig aryl amination. The hydroxide complexes were susceptible to hydrogenolysis on exposure to H-2 gas. Following H2O elimination and beta-hydride elimination of an additional cinnamyl ligand, a Pd(0) species is formed which can react with other available ligands.

AB - Palladium hydroxide dimers were prepared by reactions of CsOH with monomeric [Pd(NHC)(eta(3)-allyl)Cl] starting materials. The dimers represent species proposed as intermediates in important cross-coupling reactions. These complexes were tested for their catalytic activity in Suzuki-Miyaura coupling and Buchwald-Hartwig aryl amination. The hydroxide complexes were susceptible to hydrogenolysis on exposure to H-2 gas. Following H2O elimination and beta-hydride elimination of an additional cinnamyl ligand, a Pd(0) species is formed which can react with other available ligands.

KW - CROSS-COUPLING REACTIONS

KW - PINCER COMPLEXES

KW - BUCHWALD-HARTWIG

KW - SUZUKI-MIYAURA

KW - BONDS

KW - HYDROGENATION

KW - MONONUCLEAR

KW - HCL

U2 - 10.1021/om200579h

DO - 10.1021/om200579h

M3 - Article

SN - 0276-7333

VL - 30

SP - 4494

EP - 4496

JO - Organometallics

JF - Organometallics

IS - 17

ER -

Synthesis, Characterization, and Reactivity of N-Heterocyclic Carbene Palladium(II) Hydroxide Dimers

Abstract

Keywords

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