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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

Contributor(s):
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
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Further Information

Publication History

Publication Date:
18 February 2020 (online)

 
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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.


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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.


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Review

J. K. Stille Angew. Chem., Int. Ed. Engl. 1986, 25, 508–524.


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