11.8.4 Stille Coupling

The coupling of vinyl stannanes with vinyl halides or triflates using palladium catalysis is one of the powerful methods for the carbon-carbon bond formation (Scheme 10). It is effective under relatively neutral conditions and compatible with many functional groups. Please see section 10.5.1 for mechanism

Scheme 10

 

11.8.5 Stille Carbonylative Coupling

The coupling reaction of aryl or vinyl triflate with organostannane using palladium-catalysis in the presence of carbon monoxide and lithium chloride takes place under relatively mild conditions to give good yields of ketones (Scheme 11).

Scheme 11

Mechanism

The reaction occurs via oxidative addition, carbonyl insertion, transmetallation and reductive elimination processes (Scheme 12).

Scheme 12

Examples: