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Developing isocyanide methodology
Dissertation   Open access

Developing isocyanide methodology

Allen Chao
Doctor of Philosophy (Ph.D.), Drexel University
Aug 2018
DOI:
https://doi.org/10.17918/D8H96F
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Abstract

Chemistry Chemistry, Organic Copper Isocyanides
Isocyanides are privileged structures, found in bioactive compounds derived from natural sources and pervasive in the synthesis of pharmacologically relevant compounds. Isocyanide synthesis is, however, limited by few commercial products and a dearth of methodology that allows for their manipulation. To this end, the focus has been on pioneering new methods and substrates. The initial work concentrated on the development of conjugate addition reactions to novel oxoalkeneisocyanides, followed by finding a method to purify difficult-to-isolate isocyanides. This was proceeded by the discovery and development of the first copper-catalyzed radical addition to alkeneisocyanides which tangentially lead to a review of copper(I)-isocyanide complex spectra and structure characteristics. Lastly, applications of Asmic, a novel isocyanide building block, were explored in the synthesis of heterocyclic scaffolds.

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