Development of versatile and silver-free protocols for gold(I) catalysis

Sylvain Gaillard; Johann Bosson; Ruben S. Ramon; Pierrick Nun; Alexandra M. Z. Slawin; Steven P. Nolan

doi:10.1002/chem.201001688

Development of versatile and silver-free protocols for gold(I) catalysis

Sylvain Gaillard, Johann Bosson, Ruben S. Ramon, Pierrick Nun, Alexandra M. Z. Slawin, Steven P. Nolan

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

Abstract

The use of a versatile N-heterocyclic carbene (NHC) gold(I) hydroxide precatalyst, [Au(OH)(IPr)], (IPr = N,N'-bis(2,6-diisopropylphenyl)-imidazol-2-ylidene) permits the in situ generation of the [Au(IPr)](+) ion by simple addition of a Bronsted acid. This cationic entity is believed to be the active species in numerous catalytic reactions. H-1 NMR studies in several solvent media of the in situ generation of this [Au(IPr)](+) ion also reveal the formation of a dinuclear gold hydroxide intermediate [{Au(IPr)}(2)(mu-OH)], which is fully characterized and was tested in gold(I) catalysis.

Original language	English
Pages (from-to)	13729-13740
Number of pages	12
Journal	Chemistry - A European Journal
Volume	16
Issue number	46
Early online date	13 Oct 2010
DOIs	https://doi.org/10.1002/chem.201001688
Publication status	Published - 10 Dec 2010

Keywords

gold
homogeneous catalysis
N-heterocyclic carbenes
Gold(I)-Catalyzed Intramolecular Hydroamination
N-Heterocyclic Carbenes
Highly Efficient
Propargylic Acetates
Inorganic-Chemistry
Platinum Catalysis
Ene Reaction
C-C
Complexes
Alkynes

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10.1002/chem.201001688

Molecular assembly using gold catalysis: Molecular assembly using gold catalysis
Nolan, S. P. (PI)
EPSRC
1/01/10 → 31/12/12
Project: Standard
FUNCAT: EU FP7 ERC Advanced Grant - FUNCAT - Fundamental Studies in Organometallic Chemistry and Homogeneous Catalysis
Nolan, S. P. (PI)
European Research Council
1/01/09 → 31/12/14
Project: Standard

Cite this

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title = "Development of versatile and silver-free protocols for gold(I) catalysis",

abstract = "The use of a versatile N-heterocyclic carbene (NHC) gold(I) hydroxide precatalyst, [Au(OH)(IPr)], (IPr = N,N'-bis(2,6-diisopropylphenyl)-imidazol-2-ylidene) permits the in situ generation of the [Au(IPr)](+) ion by simple addition of a Bronsted acid. This cationic entity is believed to be the active species in numerous catalytic reactions. H-1 NMR studies in several solvent media of the in situ generation of this [Au(IPr)](+) ion also reveal the formation of a dinuclear gold hydroxide intermediate [{Au(IPr)}(2)(mu-OH)], which is fully characterized and was tested in gold(I) catalysis.",

keywords = "gold, homogeneous catalysis, N-heterocyclic carbenes, Gold(I)-Catalyzed Intramolecular Hydroamination, N-Heterocyclic Carbenes, Highly Efficient, Propargylic Acetates, Inorganic-Chemistry, Platinum Catalysis, Ene Reaction, C-C, Complexes, Alkynes",

author = "Sylvain Gaillard and Johann Bosson and Ramon, {Ruben S.} and Pierrick Nun and Slawin, {Alexandra M. Z.} and Nolan, {Steven P.}",

year = "2010",

month = dec,

day = "10",

doi = "10.1002/chem.201001688",

language = "English",

volume = "16",

pages = "13729--13740",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley & Sons, Ltd",

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TY - JOUR

T1 - Development of versatile and silver-free protocols for gold(I) catalysis

AU - Gaillard, Sylvain

AU - Bosson, Johann

AU - Ramon, Ruben S.

AU - Nun, Pierrick

AU - Slawin, Alexandra M. Z.

AU - Nolan, Steven P.

PY - 2010/12/10

Y1 - 2010/12/10

N2 - The use of a versatile N-heterocyclic carbene (NHC) gold(I) hydroxide precatalyst, [Au(OH)(IPr)], (IPr = N,N'-bis(2,6-diisopropylphenyl)-imidazol-2-ylidene) permits the in situ generation of the [Au(IPr)](+) ion by simple addition of a Bronsted acid. This cationic entity is believed to be the active species in numerous catalytic reactions. H-1 NMR studies in several solvent media of the in situ generation of this [Au(IPr)](+) ion also reveal the formation of a dinuclear gold hydroxide intermediate [{Au(IPr)}(2)(mu-OH)], which is fully characterized and was tested in gold(I) catalysis.

AB - The use of a versatile N-heterocyclic carbene (NHC) gold(I) hydroxide precatalyst, [Au(OH)(IPr)], (IPr = N,N'-bis(2,6-diisopropylphenyl)-imidazol-2-ylidene) permits the in situ generation of the [Au(IPr)](+) ion by simple addition of a Bronsted acid. This cationic entity is believed to be the active species in numerous catalytic reactions. H-1 NMR studies in several solvent media of the in situ generation of this [Au(IPr)](+) ion also reveal the formation of a dinuclear gold hydroxide intermediate [{Au(IPr)}(2)(mu-OH)], which is fully characterized and was tested in gold(I) catalysis.

KW - gold

KW - homogeneous catalysis

KW - N-heterocyclic carbenes

KW - Gold(I)-Catalyzed Intramolecular Hydroamination

KW - N-Heterocyclic Carbenes

KW - Highly Efficient

KW - Propargylic Acetates

KW - Inorganic-Chemistry

KW - Platinum Catalysis

KW - Ene Reaction

KW - C-C

KW - Complexes

KW - Alkynes

U2 - 10.1002/chem.201001688

DO - 10.1002/chem.201001688

M3 - Article

SN - 0947-6539

VL - 16

SP - 13729

EP - 13740

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 46

ER -

Development of versatile and silver-free protocols for gold(I) catalysis

Abstract

Keywords

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Projects

Molecular assembly using gold catalysis: Molecular assembly using gold catalysis

FUNCAT: EU FP7 ERC Advanced Grant - FUNCAT - Fundamental Studies in Organometallic Chemistry and Homogeneous Catalysis

Cite this