Gold–Gold Cooperation in the Addition of Methanol to Alkynes

Roithová, Jana; Janková, Štěpánka; Jašíková, Lucie; Váňa, Jiří; Hybelbauerová, Simona

doi:10.1002/ange.201204003

Cited by 31 publications

(15 citation statements)

References 53 publications

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“…Similar intermediates have recently been proposed for the addition of MeOH to alkynes. [18] Finally, protodeauration of III or IV with phenol 5 or H 2 O takes place to afford vinyl ether 6 (Scheme 5).…”

Section: Methodsmentioning

confidence: 99%

Hydrophenoxylation of Alkynes by Cooperative Gold Catalysis

et al. 2013

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Section: Methodsmentioning

confidence: 99%

Hydrophenoxylation of Alkynes by Cooperative Gold Catalysis

et al. 2013

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“…6 -9 For example, it was proposed that aurophilic interactions are important in materials science, 10 medicinal chemistry, [11][12][13][14] and catalysis. [15][16][17][18][19][20][21][22][23][24] Pyykkö and coworkers pioneered theoretical investigation of aurophilic interactions. 25 They analyzed the role of intermolecular electrostatic, induction, and dispersion interactions in the overall attraction of closed-shell Au(I)…Au(I) dimers.…”

Section: Introductionmentioning

confidence: 99%

Aurophilic Interactions in [(L)AuCl]...[(L′)AuCl] Dimers: Calibration by Experiment and Theory

et al. 2018

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Attractive metallophilic (aurophilic, argentophilic, cuprophilic, etc.) interactions play an important role in arrangement and stabilization of oligonuclear metal ion complexes. We report a combined experimental and theoretical assessment of aurophilic interactions in closed-shell gold(I) dimers. The experimental binding energies were obtained for charged [(LH)AuCl]...[(L')AuCl] dimers (L is either a phosphine or an N-heterocyclic carbene ligand) in the gas phase. These energies served for benchmarking of correlated quantum chemical calculations (CCSD(T)-calibrated SCS-MP2/CBS method) that were then applied to neutral [(L)AuCl]...[(L')AuCl] dimers. The overall attractive interactions between monomeric units are in the order of 100-165 kJ mol in the charged dimers and of 70-105 kJ mol in the corresponding neutral dimers. In the neutral dimers, pure aurophilic interactions account for 25-30 kJ mol, the dipole-dipole interactions for 30-45 kJ mol, and the L···L' "inter-ligand" dispersion interactions for 5-25 kJ mol. Energy of the aurophilic interactions is thus comparable or even larger than that of strong hydrogen bonds.

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“…The current knowledge about this problem still primarily relies on model systems, that is, the aryl diaurated species ArA C H T U N G T R E N N U N G (AuL) 2 + . [10] In connection with the gold-catalyzed spiroacetal formation of certain alkynediols, we discovered that enol ether-derived diaurated species D are formed directly if an alkynol is allowed to react with a gold catalyst in the presence of a base. The reaction can be easily applied for in situ generation of diaurated species from all common types of hydroalkoxylation substrates: 5-endo, 5-exo/6-endo, 6-exo/7-endo and intermolecular types.…”

Section: Introductionmentioning

confidence: 99%

“…[9] Nevertheless, catalytic intermediates of the gold-catalyzed hydroalkoxylation of alkynes still remain to be experimentally explored. [10] In connection with the gold-catalyzed spiroacetal formation of certain alkynediols, we discovered that enol ether-derived diaurated species D are formed directly if an alkynol is allowed to react with a gold catalyst in the presence of a base. The intermediancy of this kind of species in a catalytic hydroalkoxylation process was first suggested by Fürstner and co-workers in 2010.…”

Section: Introductionmentioning

confidence: 99%