Alkyne Trifunctionalization via Divergent Gold Catalysis: Combining π-Acid Activation, Vinyl-Gold Addition, and Redox Catalysis.
Journal
Journal of the American Chemical Society
ISSN: 1520-5126
Titre abrégé: J Am Chem Soc
Pays: United States
ID NLM: 7503056
Informations de publication
Date de publication:
17 03 2021
17 03 2021
Historique:
pubmed:
5
3
2021
medline:
27
8
2021
entrez:
4
3
2021
Statut:
ppublish
Résumé
Here we report the first example of alkyne trifunctionalization through simultaneous construction of C-C, C-O, and C-N bonds via gold catalysis. With the assistance of a γ-keto directing group, sequential gold-catalyzed alkyne hydration, vinyl-gold nucleophilic addition, and gold(III) reductive elimination were achieved in one pot. Diazonium salts were identified as both electrophiles (N source) and oxidants (C source). Vinyl-gold(III) intermediates were revealed as effective nucleophiles toward diazonium, facilitating nucleophilic addition and reductive elimination with high efficiency. The rather comprehensive reaction sequence was achieved with excellent yields (up to 95%) and broad scope (>50 examples) under mild conditions (room temperature or 40 °C).
Identifiants
pubmed: 33661619
doi: 10.1021/jacs.1c01811
pmc: PMC10270734
mid: NIHMS1906325
doi:
Substances chimiques
Alkynes
0
Diazonium Compounds
0
Vinyl Compounds
0
Gold
7440-57-5
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.
Langues
eng
Sous-ensembles de citation
IM
Pagination
4074-4082Subventions
Organisme : NIGMS NIH HHS
ID : R01 GM120240
Pays : United States
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