Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 43, Pages 12831-12837Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201002267
Keywords
catalyst stabilization; halide metathesis; halides; palladium; transmetallation
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Funding
- University of Antwerp (BOF)
- Fund for Scientific Research-Flanders (FWO-Flanders)
- Hercules Foundation
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Halide anions can increase or decrease the transmetallation rate of the Stille reaction through in situ halide metathesis. Although the influence of the halogen present in oxidative addition complexes on the transmetallation rate with organostannanes was already known, the application of in situ halide metathesis to accelerate cross-coupling reactions with organometallic reagents is not described in the literature yet. In addition a second unprecedented role of halides was discovered. Halide anions stabilize the [Pd-0(L)(2)] catalyst in Stille reactions, by means of [(PdX)-X-0(L)(2)](-) formation (X = Cl, I), hereby preventing its leaching from the catalytic cycle. Both arene (iodobenzene) and azaheteroarene (2-halopyridine, halopyrazine, 2-halopyrimidine) substrates were used.
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