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Evaluation of polymer-supported vinyltin reagents in the Stille cross-coupling reaction |
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| Authors: | Jean-Mathieu Chrétien Françoise Zammattio Erwan Le Grognec Gilles Montavon |
| Institution: | a Université de Nantes, Nantes Atlantique Universités, CNRS, Laboratoire de Synthèse Organique (LSO), UMR 6513, 2 rue de la Houssinière, BP 92208, 44322 Nantes cedex 3, France b Université de Nantes, Nantes Atlantique Universités, CNRS, Institut des Matériaux Jean Rouxel, UMR 6502, 2 rue de la Houssinière, BP 32229, 44322 Nantes cedex 3, France c Université de Nantes, Nantes Atlantique Universités, École des Mines de Nantes, CNRS, Subatech, UMR 6457, 4 rue Alfred Kastler, BP 20722, 44307 Nantes cedex 3, France |
| Abstract: | 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). |
| Keywords: | Polymer-supported vinyltins Stille cross-coupling reaction Green chemistry β-Formylvinylanion |
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