Lewis Acid-Promoted Friedel−Crafts Alkylation Reactions with α-Ketophosphate Electrophiles
作者:Austin G. Smith、Jeffrey S. Johnson
DOI:10.1021/ol100410k
日期:2010.4.16
The BF3·OEt2-promoted nucleophilic substitution of α-aryl-α-ketophosphates to afford α,α-diaryl ketone products is described. Electron-rich α-ketophosphates perform best, with electron-neutral and electron-poor substrates also tolerated. The reaction is tolerant of a range of aromatic, heteroaromatic, and nonaromatic nucleophiles, with yields ranging from 44% to 84%. Enantioenriched starting material
描述了BF 3 ·OEt 2促进的α-芳基-α-酮磷酸盐的亲核取代,以提供α,α-二芳基酮产物。富含电子的α-酮磷酸酯的性能最佳,同时还可以耐受电子中性和贫电子的底物。该反应可耐受多种芳族,杂芳族和非芳族亲核试剂,收率范围为44%至84%。富含对映体的原料产生外消旋产物,表明通过酰基carb离子的S N 1途径。