The synthesis of heterocycles has been an emerging area of chemical research considering their high importance in pharmaceuticals, material chemistry, and natural product synthesis. The development of greener methodologies by...
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...
Herein,
we demonstrated an efficient protocol for reductive alkylation
of azides/nitro compounds via a borrowing hydrogen (BH) method. By
following this protocol, selective mono- and dialkylated amines were
obtained under mild and solvent-free conditions. A series of control
experiments and deuterium-labeling experiments were performed to understand
this catalytic process. Mechanistic studies suggested that the Ir(III)–H
was the active intermediate in this reaction. KIE study revealed that
the breaking of the C–H bond of alcohol might be the rate-limiting
step. Notably, this solvent-free strategy disclosed a high TON of
around 5600. Based on kinetic studies and control experiments, a metal–ligand
cooperative mechanism was proposed.
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