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The Stille Carbonylative Cross-Coupling Reaction
A General, Selective, and Facile Method for Ketone Synthesis from Acid Chlorides and Organotin Compounds Catalyzed by Palladium.
J. Am. Chem. Soc. 1978;
18 February 2020 (online)
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.
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.
J. K. Stille Angew. Chem., Int. Ed. Engl. 1986, 25, 508–524.