The mechanism of the gold(I)-catalyzed Meyer-Schuster rearrangement of 1-phenyl-2-propyn-1-ol via 4- endo-dig cyclization

The mechanism of the gold(I)-catalyzed Meyer-Schuster rearrangement of 1-phenyl-2-propyn-1-ol via 4- endo-dig cyclization

With the aim of rationalizing the experimental counterion- and solvent-dependent reactivity in the gold(i)-catalyzed Meyer-Schuster rearrangement of 1-phenyl-2-propyn-1-ol, a computational mechanistic study unraveled the unexpected formation of a gold-oxetene intermediate via commonly unfavorable 4-...

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Veröffentlicht in:Dalton transactions : an international journal of inorganic chemistry 2021-04, Vol.50 (15), p.5154-5160
Hauptverfasser: Sorbelli, Diego, Segato, Jacopo, Del Zotto, Alessandro, Belpassi, Leonardo, Zuccaccia, Daniele, Belanzoni, Paola
Format: Artikel
Sprache:eng
Schlagworte:
Gold
Solvents
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Zusammenfassung:With the aim of rationalizing the experimental counterion- and solvent-dependent reactivity in the gold(i)-catalyzed Meyer-Schuster rearrangement of 1-phenyl-2-propyn-1-ol, a computational mechanistic study unraveled the unexpected formation of a gold-oxetene intermediate via commonly unfavorable 4-endo-dig cyclization triggered by the counterion in low polarity solvents.
ISSN:1477-9226
1477-9234
DOI:10.1039/d1dt00080b