Tetrabutylammonium salt induced denitration of nitropyridines: Synthesis of fluoro-, hydroxy-, and methoxypyridines
Tetrabutylammonium salt induced denitration of nitropyridines: Synthesis of fluoro-, hydroxy-, and methoxypyridines
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DOI：
10.1021/ol047688v
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发表时间：
2005-02-17
期刊：
影响因子：
5.2
通讯作者：
Bock, MG
中科院分区：
文献类型：
--
作者：
Kuduk, SD;DiPardo, RM;Bock, MG
报道了一种通过氟取代反应合成氟代吡啶类化合物的有效方法。该反应是介导的四丁基氟化铵（TBAF）在温和的条件下，没有过度考虑水的存在。氟代取代通常用于2-或4-硝基取代的吡啶，而3-硝基吡啶需要伴随的吸电子基团以使反应有效地进行。在温和条件下，在相应的四丁基铵物质存在下，硝基吡啶类也会发生羟基和甲氧基取代反应。
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. Nitropyriclines also undergo hydroxy- and methoxydenitration under mild conditions in the presence of the corresponding tetrabutylammonium species.