Regio -Selective C3- and N-Alkylation of Indolines in Water under Air Using Alcohols.

We disclosed a regio -selective C-H and N-H bond functionalization of indolines using alcohols in water via tandem dehydrogenation of N -heterocycles and alcohols. A diverse range of N- and C3-alkylated indolines/indoles were accessed utilizing a new cooperative iridium catalyst. The practical applicability of this methodology was demonstrated by the preparative-scale synthesis and synthesis of a psychoactive drug, N , N -dimethyltryptamine. A catalytic cycle is proposed based on several kinetic experiments, series of control experiments and density functional theory calculations.