Energetics of key Au(<scp>iii</scp>)-substrate adducts relevant to catalytic hydroarylation of alkynes

Regnacq, Matthieu; Lesage, Denis; Holmsen, Marte S. M.; Miqueu, Karinne; Bourissou, Didier; Gimbert, Yves

doi:10.1039/d3dt02393a

Dalton Trans.

2023

DOI: 10.1039/d3dt02393a

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Energetics of key Au(iii)-substrate adducts relevant to catalytic hydroarylation of alkynes

Matthieu Regnacq,

Denis Lesage,

Marte S. M. Holmsen

et al.

Abstract: (P,C)-cyclometalated Au(III) complexes have shown remarkable ability to catalyze the intermolecular hydroarylation of alkynes. An outer-sphere mechanism has been evidenced in a previous study and is confirmed here, by consideration...

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2024

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Cited by 3 publications

References 39 publications

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Gold(III) Catalysis in Ionic Liquids: The Case Study of Coumarin Synthesis

Ravera,

Martinsen Holmsen,

Sgarbossa

et al. 2024

Adv Synth Catal

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Well‐defined (P,C)‐cyclometalated Au(III) complexes proved to be able to catalyze the synthesis of coumarins by intramolecular hydroarylation of a broad range of aryl propiolates under mild and practical conditions (0.1‐2 mol% catalyst, 25‐40°C, 1‐24 hours). Use of an ionic liquid as reaction solvent allowed to drastically decrease the amount of Brönsted acid used to unlock the catalyst regeneration step. The effect of the nature of the acid additive and of the ionic liquid anion have been assessed. Preliminary results on the extension of this methodology to the cyclization of aryl propargyl ethers are also presented.

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Gold(III) Catalysis in Ionic Liquids: The Case Study of Coumarin Synthesis

Ravera,

Martinsen Holmsen,

Sgarbossa

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

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Understanding Gold‐Alkyne Activation from Bond Dissociation Energies of Gold‐Alkyne Complexes

Gatineau,

Lesage,

Guéret

et al. 2024

Eur J Org Chem

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A detailed approach into electronic effects of ligands on gold‐alkyne interactions has been carried out in the gas phase using tandem mass spectrometry. A semi‐empirical method coupled to DFT calculations was used to quantify ligands effects on Au‐CC bond strength. To this end, the critical energies of 16 [L‐Au‐hex‐3‐yne]+ complexes with different L ligands were determined through collision induced dissociation. It was observed that electron‐rich ligands destabilize the gold‐alkyne bond, whereas phosphites and carbenes strengthened it. The influence of alkyne electronic effects on the gold‐alkyne bond has also been studied by dissociation in tandem mass spectrometry on four different alkynes. In an original approach, two successive ion‐molecule reactions within the mass spectrometer were used to measure the relative affinity of gold to an alkyne by exchange reactions. The result is that the more electron‐rich the alkyne, the stronger the gold‐alkyne bond.

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Choosing between Ti(ii) and Ti(iii): selective reduction of titanocene dichloride by elemental lanthanides

Bousrez,

Harakat,

Chevreux

et al. 2024

Dalton Trans.

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Energetics of key Au(iii)-substrate adducts relevant to catalytic hydroarylation of alkynes

Abstract: (P,C)-cyclometalated Au(III) complexes have shown remarkable ability to catalyze the intermolecular hydroarylation of alkynes. An outer-sphere mechanism has been evidenced in a previous study and is confirmed here, by consideration...

Cited by 3 publications

References 39 publications

Gold(III) Catalysis in Ionic Liquids: The Case Study of Coumarin Synthesis

Gold(III) Catalysis in Ionic Liquids: The Case Study of Coumarin Synthesis

Understanding Gold‐Alkyne Activation from Bond Dissociation Energies of Gold‐Alkyne Complexes

Choosing between Ti(ii) and Ti(iii): selective reduction of titanocene dichloride by elemental lanthanides

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