Radical Spirocyclization via Organic Photoredox Catalysis Restricted; Files Only

Harris, Amber (Fall 2019)

Permanent URL: https://etd.library.emory.edu/concern/etds/7s75dd55c?locale=es
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Abstract

Spirocyclic compounds are prevalent in drugs and natural products due to their unique three-dimensional scaffold that allows for tighter binding within structurally complex proteins, but these compounds are not easily synthesized by current methods. The use of expensive and hazardous materials, such as organotin and transition metal catalysts, makes up the majority of the literature precedent for synthesizing spirocyclic compounds. As an alternative, a mild method has been developed utilizing an organic photoredox catalyst, amine reductant, and irradiation from blue LEDs to form an array of diverse spirocyclic compounds. This new methodology allows for intramolecular radical 5-exo-trig cyclization of (hetero)aryl halide starting materials producing tricyclic ring systems that contain inherent three-dimensional properties.

Table of Contents

Introduction…………………………………………………………………………1

Results and Discussion…………………………………………………………….10

Conclusion and Future Work………………………………………………………17

References………………………………………………………………………….20

Experimental……………………………………….………………………………22

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