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.
An Ir-catalyzed tandem synthesis of various N-methylated tertiary amines from three-components coupling of carbonyl compounds, amines, and methanol following reductive amination/N-methylation is reported for the first time. A wide array...
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