Mechanistic Switch in Dual Gold Catalysis of Diynes: C(sp3)-H Activation through Bifurcation-Vinylidene versus Carbene Pathways

Mechanistic Switch in Dual Gold Catalysis of Diynes: C(sp3)-H Activation through Bifurcation-Vinylidene versus Carbene Pathways

The other side of the mountain: Changing the framework of diyne systems opens up new cyclization modes for dual gold catalysis. Instead of a 5‐endo cyclization and gold vinylidenes a 6‐endo cyclization gives rise to gold‐stabilized carbenes as key intermediates for selective CH insertions.

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Veröffentlicht in:Angewandte Chemie International Edition 2013-02, Vol.52 (9), p.2593-2598
Hauptverfasser: Hansmann, Max M., Rudolph, Matthias, Rominger, Frank, Hashmi, A. Stephen K.
Format: Artikel
Sprache:eng
Schlagworte:
Activation
alkynes
Carbenes
Catalysis
computational chemistry
CH activation
dual catalysis
Gold
Insertion
Mountains
Pathways
Switches
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Zusammenfassung:The other side of the mountain: Changing the framework of diyne systems opens up new cyclization modes for dual gold catalysis. Instead of a 5‐endo cyclization and gold vinylidenes a 6‐endo cyclization gives rise to gold‐stabilized carbenes as key intermediates for selective CH insertions.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201208777