Structural and thermochemical studies of chiral nucleophilic carbenes in the Cp*RuCl(L*) (Cp* = eta(5)-C5Me5; L* = chiral nucleophilic carbene) system

J  Huang; L  Jafarpour; A C  Hillier; E D  Stevens; Steven Patrick Nolan

doi:10.1021/om010137d

Structural and thermochemical studies of chiral nucleophilic carbenes in the CpRuCl(L) (Cp* = eta(5)-C5Me5; L* = chiral nucleophilic carbene) system

J Huang, L Jafarpour, A C Hillier, E D Stevens, Steven Patrick Nolan

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

Abstract

The reaction of [Cp*RuCl](4) (1) with chiral nucleophilic carbene ligands L = 1,3-R-2-imidazol-2-ylidene (R = (R)-1-cyclohexylethy1 ((-)ICMe), (1S,2S,3S,5R)-isopinocamphenyl ((+)-I(i)PCamp), (R)-alpha -methylbenzyl ((+)IBMe)) affords the unsaturated chiral Cp*Ru(L)Cl(Cp* = eta (5)-C5Me5) complexes 2-4 in high yields. A solution calorimetric investigation in this series Clarifies the electron donor properties of these chiral ligands, and comparisons are made with other recently reported nucleophilic carbene complexes and with the widely used PCy3. Structural information from single-crystal X-ray studies for complexes 2, 3, Cp*Ru(IMes)Cl (IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene; 5), Cp*Ru(ICy)Cl (ICy = 1,3-dicyclohexylimidazol-2-ylidene; 6), and Cp*Ru(IAd)Cl (IAd = 1,3-diadamantylimidazol-2-ylidene; 7) allows for an initial quantitative treatment of steric parameters associated with these ligands.

Original language	English
Pages (from-to)	2878-2882
Number of pages	5
Journal	Organometallics
Volume	20
Issue number	13
DOIs	https://doi.org/10.1021/om010137d
Publication status	Published - 25 Jun 2001

Keywords

PALLADIUM/IMIDAZOLIUM CHLORIDE SYSTEM
N-HETEROCYCLIC CARBENES
IMIDAZOLIN-2-YLIDENE LIGANDS
HOMOGENEOUS CATALYSIS
METAL-COMPLEXES
ARYL CHLORIDES
RUTHENIUM COMPLEXES
MOIETY

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10.1021/om010137d

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@article{867791342b8c45f7b285508fe1ea21bb,

title = "Structural and thermochemical studies of chiral nucleophilic carbenes in the Cp*RuCl(L*) (Cp* = eta(5)-C5Me5; L* = chiral nucleophilic carbene) system",

abstract = "The reaction of [Cp*RuCl](4) (1) with chiral nucleophilic carbene ligands L = 1,3-R-2-imidazol-2-ylidene (R = (R)-1-cyclohexylethy1 ((-)ICMe), (1S,2S,3S,5R)-isopinocamphenyl ((+)-I(i)PCamp), (R)-alpha -methylbenzyl ((+)IBMe)) affords the unsaturated chiral Cp*Ru(L)Cl(Cp* = eta (5)-C5Me5) complexes 2-4 in high yields. A solution calorimetric investigation in this series Clarifies the electron donor properties of these chiral ligands, and comparisons are made with other recently reported nucleophilic carbene complexes and with the widely used PCy3. Structural information from single-crystal X-ray studies for complexes 2, 3, Cp*Ru(IMes)Cl (IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene; 5), Cp*Ru(ICy)Cl (ICy = 1,3-dicyclohexylimidazol-2-ylidene; 6), and Cp*Ru(IAd)Cl (IAd = 1,3-diadamantylimidazol-2-ylidene; 7) allows for an initial quantitative treatment of steric parameters associated with these ligands.",

keywords = "PALLADIUM/IMIDAZOLIUM CHLORIDE SYSTEM, N-HETEROCYCLIC CARBENES, IMIDAZOLIN-2-YLIDENE LIGANDS, HOMOGENEOUS CATALYSIS, METAL-COMPLEXES, ARYL CHLORIDES, RUTHENIUM COMPLEXES, MOIETY",

author = "J Huang and L Jafarpour and Hillier, {A C} and Stevens, {E D} and Nolan, {Steven Patrick}",

year = "2001",

month = jun,

day = "25",

doi = "10.1021/om010137d",

language = "English",

volume = "20",

pages = "2878--2882",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society (ACS)",

number = "13",

}

TY - JOUR

T1 - Structural and thermochemical studies of chiral nucleophilic carbenes in the Cp*RuCl(L*) (Cp* = eta(5)-C5Me5; L* = chiral nucleophilic carbene) system

AU - Huang, J

AU - Jafarpour, L

AU - Hillier, A C

AU - Stevens, E D

AU - Nolan, Steven Patrick

PY - 2001/6/25

Y1 - 2001/6/25

N2 - The reaction of [Cp*RuCl](4) (1) with chiral nucleophilic carbene ligands L = 1,3-R-2-imidazol-2-ylidene (R = (R)-1-cyclohexylethy1 ((-)ICMe), (1S,2S,3S,5R)-isopinocamphenyl ((+)-I(i)PCamp), (R)-alpha -methylbenzyl ((+)IBMe)) affords the unsaturated chiral Cp*Ru(L)Cl(Cp* = eta (5)-C5Me5) complexes 2-4 in high yields. A solution calorimetric investigation in this series Clarifies the electron donor properties of these chiral ligands, and comparisons are made with other recently reported nucleophilic carbene complexes and with the widely used PCy3. Structural information from single-crystal X-ray studies for complexes 2, 3, Cp*Ru(IMes)Cl (IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene; 5), Cp*Ru(ICy)Cl (ICy = 1,3-dicyclohexylimidazol-2-ylidene; 6), and Cp*Ru(IAd)Cl (IAd = 1,3-diadamantylimidazol-2-ylidene; 7) allows for an initial quantitative treatment of steric parameters associated with these ligands.

AB - The reaction of [Cp*RuCl](4) (1) with chiral nucleophilic carbene ligands L = 1,3-R-2-imidazol-2-ylidene (R = (R)-1-cyclohexylethy1 ((-)ICMe), (1S,2S,3S,5R)-isopinocamphenyl ((+)-I(i)PCamp), (R)-alpha -methylbenzyl ((+)IBMe)) affords the unsaturated chiral Cp*Ru(L)Cl(Cp* = eta (5)-C5Me5) complexes 2-4 in high yields. A solution calorimetric investigation in this series Clarifies the electron donor properties of these chiral ligands, and comparisons are made with other recently reported nucleophilic carbene complexes and with the widely used PCy3. Structural information from single-crystal X-ray studies for complexes 2, 3, Cp*Ru(IMes)Cl (IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene; 5), Cp*Ru(ICy)Cl (ICy = 1,3-dicyclohexylimidazol-2-ylidene; 6), and Cp*Ru(IAd)Cl (IAd = 1,3-diadamantylimidazol-2-ylidene; 7) allows for an initial quantitative treatment of steric parameters associated with these ligands.

KW - PALLADIUM/IMIDAZOLIUM CHLORIDE SYSTEM

KW - N-HETEROCYCLIC CARBENES

KW - IMIDAZOLIN-2-YLIDENE LIGANDS

KW - HOMOGENEOUS CATALYSIS

KW - METAL-COMPLEXES

KW - ARYL CHLORIDES

KW - RUTHENIUM COMPLEXES

KW - MOIETY

U2 - 10.1021/om010137d

DO - 10.1021/om010137d

M3 - Article

SN - 0276-7333

VL - 20

SP - 2878

EP - 2882

JO - Organometallics

JF - Organometallics

IS - 13