Highly Active Well-Defined Palladium Precatalysts for the Efficient Amination of Aryl Chlorides

Anthony Chartoire; Mathieu Lesieur; Alexandra M. Z. Slawin; Steven P. Nolan; Catherine S. J. Cazin

doi:10.1021/om2005222

Highly Active Well-Defined Palladium Precatalysts for the Efficient Amination of Aryl Chlorides

Anthony Chartoire, Mathieu Lesieur, Alexandra M. Z. Slawin, Steven P. Nolan, Catherine S. J. Cazin

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

Abstract

The efficient preparation of [Pd(Amphos)(cinnamyl)Cl)] and [Pd(Amphos)(TFA)(kappa(2)-N,C-C6H4-CH2-NMe2)] (Amphos = 4-(di-tert-butylphosphino)-N,N-dimethylaniline and TFA = trifluoroacetate), two new well-defined palladium precatalysts, is reported. These complexes prove highly active in the Buchwald-Hartwig amination reaction, allowing the coupling of a wide range of (hetero)aryl chlorides, including unactivated, neutral, and sterically hindered substrates, with a wide range of amines, including primary and secondary amines. Finally, the catalytic systems have proven efficient at low catalyst loadings ranging from 0.1 to 0.3 mol %.

Original language	English
Pages (from-to)	4432-4436
Number of pages	5
Journal	Organometallics
Volume	30
Issue number	16
Early online date	28 Jul 2011
DOIs	https://doi.org/10.1021/om2005222
Publication status	Published - 22 Aug 2011

Keywords

N-HETEROCYCLIC CARBENE
CROSS-COUPLING REACTIONS
TEMPERATURE SUZUKI-MIYAURA
LONG-LIVED CATALYSTS
BUCHWALD-HARTWIG
(NHC)PD(ALLYL)CL NHC
BOND FORMATION
RECYCLABLE CATALYSTS
ARYLBORONIC ACIDS
C-N

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title = "Highly Active Well-Defined Palladium Precatalysts for the Efficient Amination of Aryl Chlorides",

abstract = "The efficient preparation of [Pd(Amphos)(cinnamyl)Cl)] and [Pd(Amphos)(TFA)(kappa(2)-N,C-C6H4-CH2-NMe2)] (Amphos = 4-(di-tert-butylphosphino)-N,N-dimethylaniline and TFA = trifluoroacetate), two new well-defined palladium precatalysts, is reported. These complexes prove highly active in the Buchwald-Hartwig amination reaction, allowing the coupling of a wide range of (hetero)aryl chlorides, including unactivated, neutral, and sterically hindered substrates, with a wide range of amines, including primary and secondary amines. Finally, the catalytic systems have proven efficient at low catalyst loadings ranging from 0.1 to 0.3 mol %.",

keywords = "N-HETEROCYCLIC CARBENE, CROSS-COUPLING REACTIONS, TEMPERATURE SUZUKI-MIYAURA, LONG-LIVED CATALYSTS, BUCHWALD-HARTWIG, (NHC)PD(ALLYL)CL NHC, BOND FORMATION, RECYCLABLE CATALYSTS, ARYLBORONIC ACIDS, C-N",

author = "Anthony Chartoire and Mathieu Lesieur and Slawin, {Alexandra M. Z.} and Nolan, {Steven P.} and Cazin, {Catherine S. J.}",

year = "2011",

month = aug,

day = "22",

doi = "10.1021/om2005222",

language = "English",

volume = "30",

pages = "4432--4436",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society (ACS)",

number = "16",

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TY - JOUR

T1 - Highly Active Well-Defined Palladium Precatalysts for the Efficient Amination of Aryl Chlorides

AU - Chartoire, Anthony

AU - Lesieur, Mathieu

AU - Slawin, Alexandra M. Z.

AU - Nolan, Steven P.

AU - Cazin, Catherine S. J.

PY - 2011/8/22

Y1 - 2011/8/22

N2 - The efficient preparation of [Pd(Amphos)(cinnamyl)Cl)] and [Pd(Amphos)(TFA)(kappa(2)-N,C-C6H4-CH2-NMe2)] (Amphos = 4-(di-tert-butylphosphino)-N,N-dimethylaniline and TFA = trifluoroacetate), two new well-defined palladium precatalysts, is reported. These complexes prove highly active in the Buchwald-Hartwig amination reaction, allowing the coupling of a wide range of (hetero)aryl chlorides, including unactivated, neutral, and sterically hindered substrates, with a wide range of amines, including primary and secondary amines. Finally, the catalytic systems have proven efficient at low catalyst loadings ranging from 0.1 to 0.3 mol %.

AB - The efficient preparation of [Pd(Amphos)(cinnamyl)Cl)] and [Pd(Amphos)(TFA)(kappa(2)-N,C-C6H4-CH2-NMe2)] (Amphos = 4-(di-tert-butylphosphino)-N,N-dimethylaniline and TFA = trifluoroacetate), two new well-defined palladium precatalysts, is reported. These complexes prove highly active in the Buchwald-Hartwig amination reaction, allowing the coupling of a wide range of (hetero)aryl chlorides, including unactivated, neutral, and sterically hindered substrates, with a wide range of amines, including primary and secondary amines. Finally, the catalytic systems have proven efficient at low catalyst loadings ranging from 0.1 to 0.3 mol %.

KW - N-HETEROCYCLIC CARBENE

KW - CROSS-COUPLING REACTIONS

KW - TEMPERATURE SUZUKI-MIYAURA

KW - LONG-LIVED CATALYSTS

KW - BUCHWALD-HARTWIG

KW - (NHC)PD(ALLYL)CL NHC

KW - BOND FORMATION

KW - RECYCLABLE CATALYSTS

KW - ARYLBORONIC ACIDS

KW - C-N

U2 - 10.1021/om2005222

DO - 10.1021/om2005222

M3 - Article

SN - 0276-7333

VL - 30

SP - 4432

EP - 4436

JO - Organometallics

JF - Organometallics

IS - 16

ER -

Highly Active Well-Defined Palladium Precatalysts for the Efficient Amination of Aryl Chlorides

Abstract

Keywords

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