Evaluation of polymer-supported vinyltin reagents in the Stille cross-coupling reaction

The synthesis of two new polymer-supported vinyltin reagents and their use in the Stille cross-coupling reaction is reported in a concept of green chemistry. The synthesis of two new vinyltin reagents grafted on an insoluble macroporous polymer is reported. These reagents were used in the palladium-...

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Bibliographic Details
Published in:Tetrahedron letters 2007-03, Vol.48 (10), p.1781-1785
Main Authors: Chrétien, Jean-Mathieu, Mallinger, Aurélie, Zammattio, Françoise, Grognec, Erwan Le, Paris, Michaël, Montavon, Gilles, Quintard, Jean-Paul
Format: Article
Language:English
Subjects:
Chemical Sciences
Green chemistry
Polymer-supported vinyltins
Stille cross-coupling reaction
β-Formylvinylanion
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Summary:The synthesis of two new polymer-supported vinyltin reagents and their use in the Stille cross-coupling reaction is reported in a concept of green chemistry. The synthesis of two new vinyltin reagents grafted on an insoluble macroporous polymer is reported. These reagents were used in the palladium-catalyzed Stille cross-coupling reaction with aryl halides. In all reactions, the conversion of the starting aryl halide is high and the amount of organotin by-product is particularly low (at the end of the catalytic run, the amount of Sn is up to 16 ppm in the crude reaction mixture removed of the insoluble polymer, and it is less than 1 ppm in the product purified by chromatography on silica gel).
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.01.028