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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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  • E-project-032522-232710
  • 54496
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  • 2022
UN Sustainable Development Goals
Date created
  • 2022-03-25
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