Organopalladium Chemistry – The Kosugi-Migita-Stille Reaction

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 Kosugi-Migita-Stille reaction, commonly known as the Stille coupling, is the palladium-catalysed coupling of aromatic 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 transmetallation reaction (rate-determining step) with the organostannane to give an organopalladium intermediate. This complex then undergoes a reductive elimination step, giving the product and regenerating the palladium(0) catalyst.

Animations based on R. Álvarez, O.N. Faza, A.R. de Lera, D.J. Cárdenas, Adv. Synth. Catal. 349 (2007) 887-906.

C. Cordovilla, C. Bartolomé, J. M. Martínez-Ilarduya and P. Espinet, ACS Catal., 2015, 5, 3040–3053.

 

()

How useful was this page?

Click on a star to rate it!

Average rating / 5. Vote count:

No votes so far! Be the first to rate this page.

As you found this page useful...

Follow us on social media!

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]

Provided by the