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Synthesis of (α,α-difluoropropargyl)phosphonates via aldehyde-to-alkyne homologation

机译:醛-炔同系物合成(α,α-二氟炔丙基)膦酸酯

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摘要

An efficient synthetic methodology to a series of novel alkynes bearing a difluoromethylenephosphonate function via a Corey-Fuchs-type sequence starting from (diethoxyphosphoryl)difluoroacetic aldehyde is described. Dehydrobromination of the intermediate (3,3-dibromodifluoroallyl)phosphonate with potassium tert-butoxide gave rise to the corresponding bromoalkyne, whereas upon treatment with lithium base, the generation of ((diethoxyphosphoryl) difluoropropynyl)lithium has been achieved for the first time. The synthetic potential of this lithium reagent was further demonstrated by its reactions with selected electrophiles such as aldehydes, ketones, triflates, chlorophosphines, and chlorosilanes, leading to the corresponding propargyl phosphonates in good to excellent yields. However, in the case, of sterically hindered aldehydes, (α-fluoroallenyl)phosphonates were the solely isolated products.
机译:描述了从(二乙氧基磷酰基)二氟乙醛开始的经由Corey-Fuchs型序列的一系列具有二氟亚甲基膦酸酯功能的新型炔烃的有效合成方法。中间体(3,3-二溴二氟烯丙基)膦酸酯与叔丁醇钾的脱氢溴化反应生成了相应的溴炔,而在用锂碱处理后,首次实现了((二乙氧基磷酰基)二氟丙炔基)锂的生成。该锂试剂与选定的亲电子试剂(如醛,酮,三氟甲磺酸,氯膦和氯硅烷)反应进一步证明了其合成潜力,从而以良好至极好的收率生成了相应的炔丙基膦酸酯。然而,就位阻醛而言,(α-氟代烯丙基)膦酸酯是唯一分离的产物。

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