NOTE: Important charges and non-bonding electrons are shown throughout the animation except during the transition phase
Click the structures and reaction arrows to view the 3D models and animations respectively
Cis-trans isomerisation and solvent reorganisation throughout the reaction are not shown explicitly.
For simplicity animations are shown with PH3 and SnH3 instead of PR3 and SnR3 respectively.
The Carbonylative Kosugi-Migita-Stille reaction, commonly known as the carbonylative Stille coupling, is the palladium-catalysed coupling of carbon monoxide and vinylic systems using organostannanes.
The mechanism involves the oxidative addition of vinyl or aromatic triflate or halide to give a palladium intermediate, which undergoes a carbonylation reaction. The carbon monoxide first exchanges for one of the phosphines and then rapid insertion produces an acyl palladium (II) complex. Then a transmetallation reaction (rate-determining step) with the organostannane to give an organopalladium intermediate. This complex then undergoes a reductive elimination step, giving the divinyl ketone product and regenerating the palladium(0) catalyst.
J. K. Stille, Pure Appl. Chem., 1985, 57, 1771–1780.
We are sorry that this page was not useful for you!
Let us improve this page!
Tell us how we can improve this page (in your own language if you prefer)? If you would like a response, please include your email address e.g. [email protected]