Oxidant speciation and anionic ligand effects in the gold-catalyzed oxidative coupling of arenes and alkynes.


Journal

Chemical science
ISSN: 2041-6520
Titre abrégé: Chem Sci
Pays: England
ID NLM: 101545951

Informations de publication

Date de publication:
28 Sep 2019
Historique:
received: 15 05 2019
accepted: 09 07 2019
entrez: 6 12 2019
pubmed: 6 12 2019
medline: 6 12 2019
Statut: epublish

Résumé

The mechanism of the gold-catalyzed oxidative cross-coupling of arenes and alkynes has been studied in detail combining stoichiometric experiments with putative reaction intermediates and DFT calculations. Our data suggest that ligand exchange between the alkyne, the Au(i)-catalyst and the hypervalent iodine reagent is responsible for the formation of both an Au(i)-acetylide complex and a more reactive "non-symmetric" I(iii) oxidant responsible for the crucial Au(i)/Au(iii) turnover. Further, the reactivity of the

Identifiants

pubmed: 31803420
doi: 10.1039/c9sc02372k
pii: c9sc02372k
pmc: PMC6844217
doi:

Types de publication

Journal Article

Langues

eng

Pagination

8411-8420

Informations de copyright

This journal is © The Royal Society of Chemistry 2019.

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Auteurs

Manuel Hofer (M)

Department of Chemistry , University of Zürich , Winterthurerstrasse 190 , Zürich , CH-8057 , Switzerland . Email: cristina.nevado@chem.uzh.ch.

Teresa de Haro (T)

Department of Chemistry , University of Zürich , Winterthurerstrasse 190 , Zürich , CH-8057 , Switzerland . Email: cristina.nevado@chem.uzh.ch.

Enrique Gómez-Bengoa (E)

Departamento de Química Orgánica I , Universidad del Pais Vasco , Apdo 1072 , CP-20080 Donostia-San Sebastián , Spain.

Alexandre Genoux (A)

Department of Chemistry , University of Zürich , Winterthurerstrasse 190 , Zürich , CH-8057 , Switzerland . Email: cristina.nevado@chem.uzh.ch.

Cristina Nevado (C)

Department of Chemistry , University of Zürich , Winterthurerstrasse 190 , Zürich , CH-8057 , Switzerland . Email: cristina.nevado@chem.uzh.ch.

Classifications MeSH