Phenyl−Carbonyl Coupling Reactions Promoted by Samarium Diiodide and Hexamethylphosphoramide
作者:Jiann-Shyng Shiue、Mei-Huey Lin、Jim-Min Fang
DOI:10.1021/jo9702498
日期:1997.7.1
By mediation of samarium diiodide and hexamethylphosphoramide, benzaldehydes and acetophenones underwent self- and cross-couplings to give the products having linkages at the para-carbons of phenyl rings and the carbonyl groups. The phenyl- carbonyl coupling of 2,5-dimethoxybenzaldehyde generated a Sm(III)-enolate intermediate, which was trapped by alkyl halides in a stereospecific manner to give uncommon 1,4-dialkyl-2,5-cyclohexadiene-1-carboxaldehydes. The benzaldehydes bearing tethered carbonyl chains proceeded with intramolecular phenyl-carbonyl couplings to afford fused benzocycles.
BANERJI, ASOKE;NAYAK, SANDIP K., J. CHEM. RES. (S),(1989) N0, C. 314-315