Paper
Dalton Transactions
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V. Busico, G. Ciancaleoni, A. D’Amora, A. Macchioni,
F. Tarantelli and D. Zuccaccia, Chem. – Eur. J., 2014, 20,
14594–14598; (b) M. Gatto, A. Del Zotto, J. Segato and
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Zotto, F. Tarantelli and D. Zuccaccia, ACS Catal., 2016, 6,
7363–7376.
Conclusions
In conclusion, we propose here a commonly accepted mecha-
nism for gold(I)-catalyzed alkyne reactions which can also
explain the gold-catalyzed Meyer–Schuster rearrangement of
1-phenyl-2-propyn-1-ol in p-cymene showing that it accounts
for the formation of an unprecedented gold-oxetene intermedi-
ate via 4-endo-dig cyclization. This mechanism well rationalizes
the experimental reactivity which is highly dependent on both
anion and solvent effects. Our theoretical calculations give
insights into the experimental conditions that may modify the
mechanism, such as the presence of acid traces and the nature
of the solvent. This study further consolidates the use of green
solvents instead of traditional VOS in gold catalysis.9
7 G. Ciancaleoni, L. Belpassi, D. Zuccaccia, F. Tarantelli and
P. Belanzoni, ACS Catal., 2015, 5, 803–814.
8 (a) J. Schießl, J. Schulmeister, A. Doppiu, E. Wörner,
M. Rudolph, R. Karch and A. S. K. Hashmi, Adv. Synth.
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A. Doppiu, E. Wörner, M. Rudolph, R. Karch and
A. S. K. Hashmi, Adv. Synth. Catal., 2018, 360, 3949–3959;
(c) Z. Lu, T. Li, S. R. Mudshinge, B. Xu and
G. B. Hammond, Chem. Rev., 2021, DOI: 10.1021/acs.
chemrev.0c00713.
9 M. Gatto, W. Baratta, P. Belanzoni, L. Belpassi, A. Del Zotto,
F. Tarantelli and D. Zuccaccia, Green Chem., 2018, 20,
2125–2134 and reference therein.
10 A. Zhdanko and M. E. Maier, ACS Catal., 2015, 5, 5994–
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Conflicts of interest
There are no conflicts to declare.
Acknowledgements
D. S., L. B. and P. B. are grateful to the MIUR and the
University of Perugia (AMIS, “Dipartimenti di Eccellenza
2018–2022” program and “Fondo Ricerca di Base 2019”).
11 M. Gatto, A. Del Zotto, J. Segato and D. Zuccaccia,
Organometallics, 2018, 37, 4685–4691.
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