Title
Dual effect of halides in the Stille reaction: in situ halide metathesis and catalyst stabilization Dual effect of halides in the Stille reaction: in situ halide metathesis and catalyst stabilization
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Weinheim ,
Subject
Chemistry
Source (journal)
Chemistry: a European journal. - Weinheim
Volume/pages
16(2010) :43 , p. 12831-12837
ISSN
0947-6539
ISI
000284063900011
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
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 [Pd0(L)2] catalyst in Stille reactions, by means of [Pd0X(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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