Milstein D,
Stille JK.
* Colorado State University, Fort Collins, USA
A General, Selective, and Facile Method for Ketone Synthesis from Acid Chlorides and Organotin Compounds Catalyzed by Palladium.
J. Am. Chem. Soc. 1978;
100: 3636-3638
Key words
ketones - organotin - palladium catalysis - Stille-carbonylative cross-coupling
Significance
Milstein and Stille reported a high-yielding palladium-catalyzed carbonylative coupling reaction of acid chlorides and organotin reagents. The reaction is very mild, does not require inert atmosphere and shows tolerance to a wide scope of functional groups.
Comment
Notably, aryltin groups are transferred in preference to alkyltin groups. The authors also showed that a second organic group attached to the tin can be transferred, however at a notably slower rate.
Review
J. K. Stille Angew. Chem., Int. Ed. Engl. 1986, 25, 508–524.
