Showing papers by "Robert M. DiPardo published in 2005"
TL;DR: An efficient method for the synthesis of fluoropyridine via the fluorodenitration reaction is reported, which is general for 2- or 4-nitro-substituted pyridines, while 3-nitropyridine require attendant electron-withdrawing groups for the reaction to proceed efficiently.
69 citations
TL;DR: Substituent effects on the thioimidate cyclopropane rearrangement and factors affecting regioselectivity are reported in this paper, where Palladium-mediated coupling of the pyrrolothiomethylimidate rearrangements products with Grignard reagents provides diary l pyrrlines in good yields.
10 citations
TL;DR: In this article, an efficient method for the synthesis of fluoropyridines via the fluorodenitration reaction is reported, mediated by tetrabutylammonium fluoride (TBAF) under mild conditions without undue regard to the presence of water.
Abstract: An efficient method for the synthesis of fluoropyridines via the fluorodenitration reaction is reported. The reaction is mediated by tetrabutylammonium fluoride (TBAF) under mild conditions without undue regard to the presence of water. The fluorodenitration is general for 2- or 4-nitro-substituted pyridines, while 3-nitropyridines require attendant electron-withdrawing groups for the reaction to proceed efficiently. Nitropyridines also undergo hydroxy- and methoxydenitration under mild conditions in the presence of the corresponding tetrabutylammonium species. [reaction: see text]
3 citations