Novel Methodology Towards the Indole Core and Iron-Catalyzed Electrophilic Hydroamination of Alkenes
Abstract
Indole-containing structures and their generation still draw much attention
because of their ubiquity in natural products, medicinal compounds, and organic
materials. Given this prevalence, synthetic methods toward these structural motifs are
numerous, each with a distinct set of advantages and disadvantages. One significant
challenge is the generation of 3,3-disubstituted indolines that are frequently encountered
in indole cores. The discovery, optimization, and scope of a C3-quaternary indolenine
synthesis, as well as, efforts to expand the methodology for the generation of higher
order indole-containing polycycles, will be discussed. This novel reactivity also lead to
a generalized synthesis of α,β-unsaturated N-aryl ketonitrones which has few literature
examples. A modest start to realizing the success of 3-substituted non-N-protected
indoles as a Michael donor will also be explored.
Green chemistry continues to play an important role in creating a sustainable
world. At the core of green chemistry is the reduction or elimination of the use or
generation of hazardous substances. Catalysis by definition is green by reduction;
however, many of the catalytic systems utilize toxic metals that can hamper or cause
further concerns with allowable limits on industrial scales. Iron catalyzed reactions seek
to replace these toxic metals with a benign one that is also relatively cheap. Nitrogen
containing compounds are an important feed stock for the pharmaceutical and other
industries. The iron catalyzed intermolecular hydroamination of alkenes with
electrophilic amines will be discussed.
Subject
indoleindolenine
nitrone
pyrroloindoline
hydrocarbazole
conjugate addition
iron
amination
hydroamination
Citation
Huehls, Christopher Bryan (2014). Novel Methodology Towards the Indole Core and Iron-Catalyzed Electrophilic Hydroamination of Alkenes. Doctoral dissertation, Texas A & M University. Available electronically from https : / /hdl .handle .net /1969 .1 /152597.