Fe-catalyzed decarbonylative cascade reaction of N-aryl cinnamamides with aliphatic aldehydes to construct 3,4-dihydroquinolin-2(1H)-ones

A practical Fe-catalyzed decarbonylative cascade reaction of N-aryl cinnamamides with aliphatic aldehydes to provide C3 alkylated 3,4-dihydroquinolin-2(1H)-ones is developed. Aliphatic aldehydes were oxidative decarbonylated into 1o, 2o and 3o alkyl radicals conveniently and allows for the subsequent cascade construction of C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds via radical addition and HAS-type cyclization. The importance of the amide linkage and the selectivity of 6-endo-trig over 5-exo-trig cyclization pathway were elucidated by experimental results and DFT calculations.