Lewis Acid Enhancement of Gold Catalytic Activity Through Counterion Coordination. Synthesis of Benzofulvenes from Progargylsilanes and Benzophenones

A simple, regioselective and high yielding gold‐catalyzed synthesis of benzofulvenes, from progargylsilanes and benzophenones, is described. Initially, the carbonyl compound is synergistically activated by the silyl moiety and, for the cyclization step, the gold catalytic activity is clearly increas...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2022-03, Vol.364 (7), p.1286-1294
Main Authors: Fernández, Sergio, Santamaría, Javier, Ballesteros, Alfredo
Format: Article
Language:English
Subjects:
Activated carbon
Aluminum
Aluminum chloride
Anions
Carbonyl compounds
Carbonyls
Catalytic activity
Chemical synthesis
Chlorides
Coordination
Gold
Homogeneous catalysis
Lewis acid
Lewis acids
Synthetic methods
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Summary:A simple, regioselective and high yielding gold‐catalyzed synthesis of benzofulvenes, from progargylsilanes and benzophenones, is described. Initially, the carbonyl compound is synergistically activated by the silyl moiety and, for the cyclization step, the gold catalytic activity is clearly increased by the participation of aluminum trichloride, acting as a cocatalyst. Several mechanistic intermediates, such as enynes and silylbenzofulvenes, have been isolated. Different control experiments have been performed, indicating the participation of [LAu][NTf2AlCl3] complex as the true catalyst, and revealing a dramatic enhancement of the gold activity by coordination of the Lewis acid to the gold counterion.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202200165