Catalytic dehalogenation of aryl halides mediated by a palladium/imidazolium salt system

M S  Viciu; G A  Grasa; Steven Patrick Nolan

doi:10.1021/om010332s

Catalytic dehalogenation of aryl halides mediated by a palladium/imidazolium salt system

M S Viciu, G A Grasa, Steven Patrick Nolan

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

Abstract

A convenient and efficient catalytic aryl halide dehalogenation protocol has been developed using an imidazolium salt/palladium/base system. The use of the ligand precursor SIMes . HCl ((2,4,6-trimethylphenyl)dihydroimidazolium chloride) in conjunction with Pd(dba)2 was found to be most effective for the dehalogenation of aryl chlorides, bromides, and polyhalogenated aromatic hydrocarbons. Strong bases having beta -hydrogens both perform deprotonation of the imidazolium salt and are hydrogen sources for the dehalogenation process. The oxidative addition of the imidazolium salt to the palladium(0) precursor generating a carbene palladium hydride species may also be involved in the dehalogenation process. This oxidative-addition reaction may have fundamental implications in low-valent metal carbene mediated transformations.

Original language	English
Pages (from-to)	3607-3612
Number of pages	6
Journal	Organometallics
Volume	20
Issue number	16
DOIs	https://doi.org/10.1021/om010332s
Publication status	Published - 6 Aug 2001

Keywords

OLEFIN METATHESIS CATALYSTS
N-HETEROCYCLIC CARBENES
CROSS-COUPLING REACTION
ORGANIC HALIDES
ARYLBORONIC ACIDS
AROMATIC HALIDES
REDUCTIVE DEHALOGENATION
TRANSFER HYDROGENOLYSIS
NICKEL-COMPLEXES
SODIUM HYDRIDE

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@article{003e7aa803a3465fa601a0d47d48a8e6,

title = "Catalytic dehalogenation of aryl halides mediated by a palladium/imidazolium salt system",

abstract = "A convenient and efficient catalytic aryl halide dehalogenation protocol has been developed using an imidazolium salt/palladium/base system. The use of the ligand precursor SIMes . HCl ((2,4,6-trimethylphenyl)dihydroimidazolium chloride) in conjunction with Pd(dba)2 was found to be most effective for the dehalogenation of aryl chlorides, bromides, and polyhalogenated aromatic hydrocarbons. Strong bases having beta -hydrogens both perform deprotonation of the imidazolium salt and are hydrogen sources for the dehalogenation process. The oxidative addition of the imidazolium salt to the palladium(0) precursor generating a carbene palladium hydride species may also be involved in the dehalogenation process. This oxidative-addition reaction may have fundamental implications in low-valent metal carbene mediated transformations.",

keywords = "OLEFIN METATHESIS CATALYSTS, N-HETEROCYCLIC CARBENES, CROSS-COUPLING REACTION, ORGANIC HALIDES, ARYLBORONIC ACIDS, AROMATIC HALIDES, REDUCTIVE DEHALOGENATION, TRANSFER HYDROGENOLYSIS, NICKEL-COMPLEXES, SODIUM HYDRIDE",

author = "Viciu, {M S} and Grasa, {G A} and Nolan, {Steven Patrick}",

year = "2001",

month = aug,

day = "6",

doi = "10.1021/om010332s",

language = "English",

volume = "20",

pages = "3607--3612",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society (ACS)",

number = "16",

}

TY - JOUR

T1 - Catalytic dehalogenation of aryl halides mediated by a palladium/imidazolium salt system

AU - Viciu, M S

AU - Grasa, G A

AU - Nolan, Steven Patrick

PY - 2001/8/6

Y1 - 2001/8/6

N2 - A convenient and efficient catalytic aryl halide dehalogenation protocol has been developed using an imidazolium salt/palladium/base system. The use of the ligand precursor SIMes . HCl ((2,4,6-trimethylphenyl)dihydroimidazolium chloride) in conjunction with Pd(dba)2 was found to be most effective for the dehalogenation of aryl chlorides, bromides, and polyhalogenated aromatic hydrocarbons. Strong bases having beta -hydrogens both perform deprotonation of the imidazolium salt and are hydrogen sources for the dehalogenation process. The oxidative addition of the imidazolium salt to the palladium(0) precursor generating a carbene palladium hydride species may also be involved in the dehalogenation process. This oxidative-addition reaction may have fundamental implications in low-valent metal carbene mediated transformations.

AB - A convenient and efficient catalytic aryl halide dehalogenation protocol has been developed using an imidazolium salt/palladium/base system. The use of the ligand precursor SIMes . HCl ((2,4,6-trimethylphenyl)dihydroimidazolium chloride) in conjunction with Pd(dba)2 was found to be most effective for the dehalogenation of aryl chlorides, bromides, and polyhalogenated aromatic hydrocarbons. Strong bases having beta -hydrogens both perform deprotonation of the imidazolium salt and are hydrogen sources for the dehalogenation process. The oxidative addition of the imidazolium salt to the palladium(0) precursor generating a carbene palladium hydride species may also be involved in the dehalogenation process. This oxidative-addition reaction may have fundamental implications in low-valent metal carbene mediated transformations.

KW - OLEFIN METATHESIS CATALYSTS

KW - N-HETEROCYCLIC CARBENES

KW - CROSS-COUPLING REACTION

KW - ORGANIC HALIDES

KW - ARYLBORONIC ACIDS

KW - AROMATIC HALIDES

KW - REDUCTIVE DEHALOGENATION

KW - TRANSFER HYDROGENOLYSIS

KW - NICKEL-COMPLEXES

KW - SODIUM HYDRIDE

U2 - 10.1021/om010332s

DO - 10.1021/om010332s

M3 - Article

SN - 0276-7333

VL - 20

SP - 3607

EP - 3612

JO - Organometallics

JF - Organometallics

IS - 16

ER -

Catalytic dehalogenation of aryl halides mediated by a palladium/imidazolium salt system

Abstract

Keywords

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