Rerouting nucleophilic substitution from the 4-position to the 2- or 6-position of 2,4-dihalopyridines and 2,4,6-trihalopyridines: the solution to a long-standing problem |
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Authors: | Schlosser Manfred Rausis Thierry Bobbio Carla |
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Institution: | Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale, BCh, CH-1015 Lausanne, Switzerland. manfred.schlosser@epfl.ch |
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Abstract: | 2,4-Difluoro-, 2,4,6-trifluoro-, and 2,3,4,6-tetrafluoropyridine undergo nucleophilic substitution preferentially if not exclusively at the 4-position. However, after the introduction of a trialkylsilyl group at C-3 or C-5, the halogen at the 6-(2-)position is displaced selectively. This synthetically valuable regiocontrol can also be realized with other halopyridines such as 2,4-dichloro- and 2,4,6-trichloropyridine. |
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