Simple synthesis of CpNi(NHC)Cl complexes (Cp = cyclopentadienyl; NHC=N-heterocyclic carbene)

RA Kelly; NM Scott; S Diez-Gonzalez; ED Stevens; Steven Patrick Nolan

doi:10.1021/om0501879

Simple synthesis of CpNi(NHC)Cl complexes (Cp = cyclopentadienyl; NHC=N-heterocyclic carbene)

RA Kelly, NM Scott, S Diez-Gonzalez, ED Stevens, Steven Patrick Nolan

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

166 Citations (Scopus)

Abstract

The reaction of saturated and unsaturated imidazolium salts with nickelocene in refluxing THF results in the formation of NHC complexes of general formula CpNi(NHC)Cl (NHC = SIMes (2), IPr (3), SIPr (4)). This protonation Of CP2Ni was also tested using phosphonium salts, and the reaction of nickelocene with triethylphosphonium chloride leads to CpNi(PEt3)Cl (5). All compounds were characterized by NMR and X-ray crystallography. The catalytic activity of the NHC compounds was tested in aryl amination (Buchwald-Hartwig reaction) and in aryl halide dehalogenation reactions.

Original language	English
Pages (from-to)	3442-3447
Number of pages	6
Journal	Organometallics
Volume	24
Issue number	14
DOIs	https://doi.org/10.1021/om0501879
Publication status	Published - 4 Jul 2005

Keywords

PALLADIUM-CATALYZED AMINATION
TRANSITION-METAL-COMPLEXES
ARYL CHLORIDES
HYDROSILYLATION CATALYSTS
TRANSFER HYDROGENATION
STABLE CARBENES
LIGAND
ALDEHYDES
BOND
ELIMINATION

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title = "Simple synthesis of CpNi(NHC)Cl complexes (Cp = cyclopentadienyl; NHC=N-heterocyclic carbene)",

abstract = "The reaction of saturated and unsaturated imidazolium salts with nickelocene in refluxing THF results in the formation of NHC complexes of general formula CpNi(NHC)Cl (NHC = SIMes (2), IPr (3), SIPr (4)). This protonation Of CP2Ni was also tested using phosphonium salts, and the reaction of nickelocene with triethylphosphonium chloride leads to CpNi(PEt3)Cl (5). All compounds were characterized by NMR and X-ray crystallography. The catalytic activity of the NHC compounds was tested in aryl amination (Buchwald-Hartwig reaction) and in aryl halide dehalogenation reactions.",

keywords = "PALLADIUM-CATALYZED AMINATION, TRANSITION-METAL-COMPLEXES, ARYL CHLORIDES, HYDROSILYLATION CATALYSTS, TRANSFER HYDROGENATION, STABLE CARBENES, LIGAND, ALDEHYDES, BOND, ELIMINATION",

author = "RA Kelly and NM Scott and S Diez-Gonzalez and ED Stevens and Nolan, {Steven Patrick}",

year = "2005",

month = jul,

day = "4",

doi = "10.1021/om0501879",

language = "English",

volume = "24",

pages = "3442--3447",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society (ACS)",

number = "14",

}

TY - JOUR

T1 - Simple synthesis of CpNi(NHC)Cl complexes (Cp = cyclopentadienyl; NHC=N-heterocyclic carbene)

AU - Kelly, RA

AU - Scott, NM

AU - Diez-Gonzalez, S

AU - Stevens, ED

AU - Nolan, Steven Patrick

PY - 2005/7/4

Y1 - 2005/7/4

N2 - The reaction of saturated and unsaturated imidazolium salts with nickelocene in refluxing THF results in the formation of NHC complexes of general formula CpNi(NHC)Cl (NHC = SIMes (2), IPr (3), SIPr (4)). This protonation Of CP2Ni was also tested using phosphonium salts, and the reaction of nickelocene with triethylphosphonium chloride leads to CpNi(PEt3)Cl (5). All compounds were characterized by NMR and X-ray crystallography. The catalytic activity of the NHC compounds was tested in aryl amination (Buchwald-Hartwig reaction) and in aryl halide dehalogenation reactions.

AB - The reaction of saturated and unsaturated imidazolium salts with nickelocene in refluxing THF results in the formation of NHC complexes of general formula CpNi(NHC)Cl (NHC = SIMes (2), IPr (3), SIPr (4)). This protonation Of CP2Ni was also tested using phosphonium salts, and the reaction of nickelocene with triethylphosphonium chloride leads to CpNi(PEt3)Cl (5). All compounds were characterized by NMR and X-ray crystallography. The catalytic activity of the NHC compounds was tested in aryl amination (Buchwald-Hartwig reaction) and in aryl halide dehalogenation reactions.

KW - PALLADIUM-CATALYZED AMINATION

KW - TRANSITION-METAL-COMPLEXES

KW - ARYL CHLORIDES

KW - HYDROSILYLATION CATALYSTS

KW - TRANSFER HYDROGENATION

KW - STABLE CARBENES

KW - LIGAND

KW - ALDEHYDES

KW - BOND

KW - ELIMINATION

UR - http://www.scopus.com/inward/record.url?scp=22444440761&partnerID=8YFLogxK

U2 - 10.1021/om0501879

DO - 10.1021/om0501879

M3 - Article

SN - 0276-7333

VL - 24

SP - 3442

EP - 3447

JO - Organometallics

JF - Organometallics

IS - 14

ER -

Simple synthesis of CpNi(NHC)Cl complexes (Cp = cyclopentadienyl; NHC=N-heterocyclic carbene)

Abstract

Keywords

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