A Novel C-H Cyanation Strategy in Organic Chemistry

Tabit, Hana

Student Work

A Novel C-H Cyanation Strategy in Organic Chemistry

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Due to the stability of fully substituted C-H bonds, aliphatic C(sp)3 sites are not easily accessed. Using an adaptation of novel photoredox catalyzed C-H functionalization methods developed by the Musacchio Group, this project explores the design and optimization of a selective cyanation reaction. The relevance of the photocatalyst, solvent, abstractor, and CN-source properties are investigated alongside variables such as time and temperature. Combined yields of isomers 1-adamantanecarbonitrile and 2-adamantanecarbonitrile demonstrate 59% cyanation capability using best conditions. There is much more to expand upon in this reaction, but novel photoredox catalysis methods successfully cyanate tertiary C-H positions on an aliphatic substrate, and may be promising to the field of late stage functionalization.

This report represents the work of one or more WPI undergraduate students submitted to the faculty as evidence of completion of a degree requirement. WPI routinely publishes these reports on its website without editorial or peer review.

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