N-Heterocyclic Carbenes (NHCs) Containing N-C-Palladacycle Complexes: Synthesis and Reactivity in Aryl Amination Reactions

Julie Broggi; Herve Clavier; Steven Patrick Nolan

doi:10.1021/om8006689

N-Heterocyclic Carbenes (NHCs) Containing N-C-Palladacycle Complexes: Synthesis and Reactivity in Aryl Amination Reactions

Julie Broggi, Herve Clavier, Steven Patrick Nolan

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

Abstract

Starting from the corresponding dimer, new saturated NHC-containing N,N-dimethyl biphenylamine (DMBPA) palladacycle complexes have been synthesized and fully characterized. Catalytic activity of these well-defined, air- and moisture-stable palladium(II) complexes was evaluated in the Buchwald-Hartwig amination involving a range of unactivated aryl chlorides. From a practical perspective, the reaction conditions required when using [(NHC)Pd(palladacycle)Cl] systems are very appealing. The organic biphenyl ligand used in the synthesis of the pallaclacycles has been synthesized using a Suzuki-Miyaura cross-coupling employing the novel palladacycle-NHC complexes.

Original language	English
Pages (from-to)	5525-5531
Number of pages	7
Journal	Organometallics
Volume	27
Issue number	21
DOIs	https://doi.org/10.1021/om8006689
Publication status	Published - 10 Nov 2008

Keywords

CROSS-COUPLING REACTIONS
PALLADIUM-CATALYZED AMINATION
ROOM-TEMPERATURE
SUZUKI-MIYAURA
(NHC)PD(ALLYL)CL NHC
HECK REACTION
PHOSPHA-PALLADACYCLES
HOMOGENEOUS CATALYSIS
OLEFIN METATHESIS
BUCHWALD-HARTWIG

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10.1021/om8006689

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title = "N-Heterocyclic Carbenes (NHCs) Containing N-C-Palladacycle Complexes: Synthesis and Reactivity in Aryl Amination Reactions",

abstract = "Starting from the corresponding dimer, new saturated NHC-containing N,N-dimethyl biphenylamine (DMBPA) palladacycle complexes have been synthesized and fully characterized. Catalytic activity of these well-defined, air- and moisture-stable palladium(II) complexes was evaluated in the Buchwald-Hartwig amination involving a range of unactivated aryl chlorides. From a practical perspective, the reaction conditions required when using [(NHC)Pd(palladacycle)Cl] systems are very appealing. The organic biphenyl ligand used in the synthesis of the pallaclacycles has been synthesized using a Suzuki-Miyaura cross-coupling employing the novel palladacycle-NHC complexes.",

keywords = "CROSS-COUPLING REACTIONS, PALLADIUM-CATALYZED AMINATION, ROOM-TEMPERATURE, SUZUKI-MIYAURA, (NHC)PD(ALLYL)CL NHC, HECK REACTION, PHOSPHA-PALLADACYCLES, HOMOGENEOUS CATALYSIS, OLEFIN METATHESIS, BUCHWALD-HARTWIG",

author = "Julie Broggi and Herve Clavier and Nolan, {Steven Patrick}",

year = "2008",

month = nov,

day = "10",

doi = "10.1021/om8006689",

language = "English",

volume = "27",

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journal = "Organometallics",

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T1 - N-Heterocyclic Carbenes (NHCs) Containing N-C-Palladacycle Complexes: Synthesis and Reactivity in Aryl Amination Reactions

AU - Broggi, Julie

AU - Clavier, Herve

AU - Nolan, Steven Patrick

PY - 2008/11/10

Y1 - 2008/11/10

N2 - Starting from the corresponding dimer, new saturated NHC-containing N,N-dimethyl biphenylamine (DMBPA) palladacycle complexes have been synthesized and fully characterized. Catalytic activity of these well-defined, air- and moisture-stable palladium(II) complexes was evaluated in the Buchwald-Hartwig amination involving a range of unactivated aryl chlorides. From a practical perspective, the reaction conditions required when using [(NHC)Pd(palladacycle)Cl] systems are very appealing. The organic biphenyl ligand used in the synthesis of the pallaclacycles has been synthesized using a Suzuki-Miyaura cross-coupling employing the novel palladacycle-NHC complexes.

AB - Starting from the corresponding dimer, new saturated NHC-containing N,N-dimethyl biphenylamine (DMBPA) palladacycle complexes have been synthesized and fully characterized. Catalytic activity of these well-defined, air- and moisture-stable palladium(II) complexes was evaluated in the Buchwald-Hartwig amination involving a range of unactivated aryl chlorides. From a practical perspective, the reaction conditions required when using [(NHC)Pd(palladacycle)Cl] systems are very appealing. The organic biphenyl ligand used in the synthesis of the pallaclacycles has been synthesized using a Suzuki-Miyaura cross-coupling employing the novel palladacycle-NHC complexes.

KW - CROSS-COUPLING REACTIONS

KW - PALLADIUM-CATALYZED AMINATION

KW - ROOM-TEMPERATURE

KW - SUZUKI-MIYAURA

KW - (NHC)PD(ALLYL)CL NHC

KW - HECK REACTION

KW - PHOSPHA-PALLADACYCLES

KW - HOMOGENEOUS CATALYSIS

KW - OLEFIN METATHESIS

KW - BUCHWALD-HARTWIG

UR - http://www.scopus.com/inward/record.url?scp=56049123633&partnerID=8YFLogxK

U2 - 10.1021/om8006689

DO - 10.1021/om8006689

M3 - Article

SN - 0276-7333

VL - 27

SP - 5525

EP - 5531

JO - Organometallics

JF - Organometallics

IS - 21

ER -

N-Heterocyclic Carbenes (NHCs) Containing N-C-Palladacycle Complexes: Synthesis and Reactivity in Aryl Amination Reactions

Abstract

Keywords

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