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The Development and Catalytic Uses of N-Heterocyclic Carbene Gold Complexes

https://doi.org/10.1021/ar1000764
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[(NHC)Au<sup>I</sup>]-Catalyzed Rearrangement of Allylic Acetates
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[(NHC)Au<sup>I</sup>]-Catalyzed Acid-Free Alkyne Hydration at Part-per-Million Catalyst Loadings
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Effective transformation of unactivated alkynes into ketones or acetals with a gold(III) catalyst
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Isolable Gold(I) Complexes Having One Low-Coordinating Ligand as Catalysts for the Selective Hydration of Substituted Alkynes at Room Temperature without Acidic Promoters
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Gold(I)-Catalyzed Intermolecular Addition of Carbon Nucleophiles to 1,5- and 1,6-Enynes
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Gold Activation of Nitriles: Catalytic Hydration to Amides
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A N-heterocyclic carbene gold hydroxide complex: a golden synthon
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Gold(I)-Mediated C−H Activation of Arenes
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Synthesis, Structures, and Excited‐State Geometries of Alkynylgold(I) Complexes
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Carboxylation of C−H Bonds Using <i>N</i>-Heterocyclic Carbene Gold(I) Complexes
resolves10.1021/ol062107i
Room Temperature Hydroamination of<i>N</i>-Alkenyl Ureas Catalyzed by a Gold(I)<i>N</i>-Heterocyclic Carbene Complex
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Intermolecular Hydroamination of Allenes with <i>N</i>-Unsubstituted Carbamates Catalyzed by a Gold(I) <i>N</i>-Heterocyclic Carbene Complex
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Regio- and Stereoselective Synthesis of Alkyl Allylic Ethers via Gold(I)-Catalyzed Intermolecular Hydroalkoxylation of Allenes with Alcohols
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Synthesis of Substituted 1,2-Dihydroquinolines and Quinolines from Aromatic Amines and Alkynes by Gold(I)-Catalyzed Tandem Hydroamination−Hydroarylation under Microwave-Assisted Conditions
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Intermolecular Reaction of Internal Alkynes and Imines: Propargyl Tosylates as Key Partners in a Gold-Catalyzed [4 + 1] Unusual Cyclization Leading to Cyclopent-2-enimines
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NHC-Stabilized Gold(I) Complexes: Suitable Catalysts for 6-<i>exo</i>-dig Heterocyclization of 1-(<i>o</i>-Ethynylaryl)ureas
resolves10.1021/ol902675k
Regioselective Synthesis of <i>tert</i>-Allylic Ethers via Gold(I)-Catalyzed Intermolecular Hydroalkoxylation of Allenes
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Gold(I)-Catalyzed Oxidative Rearrangements
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Stabilization of Organometallic Species Achieved by the Use of N‐Heterocyclic Carbene (NHC) Ligands
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Reactions of a Stable Monomeric Gold(I) Hydride Complex
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Structure and Bonding in Neutral and Cationic 14‐Electron Gold Alkyne π Complexes
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Steering the Surprisingly Modular π‐Acceptor Properties of N‐Heterocyclic Carbenes: Implications for Gold Catalysis
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Synthesis and Characterization of Gold(I) <i>N</i>-Heterocyclic Carbene Complexes Bearing Biologically Compatible Moieties
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Anticancer and Antimicrobial Metallopharmaceutical Agents Based on Palladium, Gold, and Silver N-Heterocyclic Carbene Complexes
The 22 references without a DOI — listed, not checked
no DOI — not checkedNumerous reviews recently published in two thematic issues, see:
no DOI — not checkedFor reviews on the use of gold in homogeneous catalysis, see:
no DOI — not checkedFor recent reviews on coinage metal in catalysis, see:
no DOI — not checkedref4/cit4c
no DOI — not checkedaAt the offset of this project in 2004, only one report describing the catalytic activity of a NHC-Au complex had been published:
no DOI — not checkedbIt should also be noted that, prior to this date, Teles and co-workers mentioned the use of NHCs for the hydroalkoxylation of alkynes. Nevertheless, it is only the subject of a footnote and no experimental details were given, see:
no DOI — not checkedbFor an early synthesis of [Au(IMes)Cl], see:
no DOI — not checkedUse of the other commonly encountered gold precursor, [Au(THT)Cl] (THT= tetrahydrothiophene), is also a viable synthetic route leading to the [Au(NHC)Cl] complexes.
no DOI — not checkedbFor the isolation of a [Au(PR3)(L)]+A-(L = ligand) complex, see:
no DOI — not checkedThe interest in this chemistry—now spanning some 35 years—continues at Firmenich under the direction of Dr. Charles Fehr; see:
no DOI — not checkedbFor an early report on sigmatropic rearrangement and its mechanism, see the seminal work of Overman:
no DOI — not checkedbFor a recent report describing an updated mechanism, see:
no DOI — not checkedref24/cit24ba
no DOI — not checkedbFor an original report on hydration of alkyne, see:
no DOI — not checkedFor phosphine-bearing analogues:
no DOI — not checkedaReference(9).
no DOI — not checkedbFor a general protocol to generate the putative [Au(NHC)]+species without the use of silver additives, see:
no DOI — not checkedref32/cit32ba
no DOI — not checkedShortly after our report, a disclosure on the use of gold for C−H activation of fluoroarene C−H bonds appeared:
no DOI — not checkedref34/cit34
no DOI — not checkedFor synthesis and properties of [Au(NHC)(alkynyl)] complexes, see, for example,
no DOI — not checkedComplex1is commercially available as a white air and moisture stable solid from Strem and Aldrich.
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