Photoinduced 1,4-additions of indoles to enones.
[reaction: see text] A photoinduced procedure for the 1,4-addition of indoles to enones is described. This reaction occurs with modest to excellent yield for cyclic and some acyclic enones. This reaction is experimentally simple, requiring only irradiation (UVA lamps, ca. 350 nm) of the reagents in a CH2Cl2 solution at room temperature, and avoids the necessity to use a Lewis acid. An important solvent effect was noticed, with CH2Cl2 and CHCl3 being the optimal solvents. Various substituents are tolerated on the indole moiety and an electronic trend was noticed, as electron-withdrawing groups can suppress this reaction. A mechanism involving single electron transfer between the enone triplet excited state and the indole is proposed and accounts for all experimental observations.
Moran
Joseph
J
Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5.
Suen
Tanya
T
Beauchemin
André M
AM