Issue 15, 2021
From the journal:

Dalton Transactions

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

Diego Sorbelli, ORCID logo a   Jacopo Segato,b   Alessandro Del Zotto, ORCID logo b   Leonardo Belpassi, ORCID logo c   Daniele Zuccaccia ORCID logo *b  and  Paola Belanzoni ORCID logo *ac  

* Corresponding authors

a Department of Chemistry, Biology and Biotechnology, University of Perugia, Via Elce di Sotto 8, Perugia, Italy
E-mail: paola.belanzoni@unipg.it

b Dipartimento di Scienze Agroalimentari, Ambientali e Animali, Sezione di Chimica, Università di Udine, Via Cotonificio 108, Udine, Italy
E-mail: daniele.zuccaccia@uniud.it

c Institute of Chemical Sciences and Technologies “Giulio Natta” of CNR (CNR-SCITEC), c/o Department of Chemistry, Biology and Biotechnology, University of Perugia, Via Elce di Sotto 8, Perugia, Italy

Abstract

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.

Graphical abstract: The mechanism of the gold(i)-catalyzed Meyer–Schuster rearrangement of 1-phenyl-2-propyn-1-ol via 4-endo-dig cyclization

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Article information

DOI
https://doi.org/10.1039/D1DT00080B
Article type
Paper
Submitted
09 Jan 2021
Accepted
25 Feb 2021
First published
26 Feb 2021

Dalton Trans., 2021,50, 5154-5160

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

D. Sorbelli, J. Segato, A. Del Zotto, L. Belpassi, D. Zuccaccia and P. Belanzoni, Dalton Trans., 2021, 50, 5154 DOI: 10.1039/D1DT00080B

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