Fluorine-Assisted Selective Alkylation to Fluorinated Epoxides and Carbonyl Compounds: Implication of Pentacoordinate Trialkylaluminum Complexes

摘要

Our concept is also applicable to the selective alkylation of carbonyl compounds with organoaluminum reagents. Indeed, treatment of an equimolar mixture of 2-fluorobenzaldehyde and 4-fluorobenzaldehyde in toluene at -78 deg C with Me_2AlC≡CPh (1 equiv) resulted in formation of two different propargyl alcohols 6 and 7 (X=F, R=Ph; 58/100 combined yield) in a ratio of 9.2:1.