Synfacts 2020; 16(03): 0314
DOI: 10.1055/s-0039-1690358
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

The Stille Carbonylative Cross-Coupling Reaction

Mark Lautens
Randy Sanichar
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
Further Information

Publication History

Publication Date:
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.