Carbon-Carbon Bonds Formed by Lewis Acid Catalysis or Photoactivation

Methods to generate C¬–C bonds are of great interest to synthetic organic chemists. Ideally, these reactions will be simple, robust, and catalytic. Herein is described the synthesis of tertiary and all-carbon quaternary centers from propargylic alcohols, organoboronates, and Lewis acids. Lewis acids can also be used to facilitate a mild Friedel-Crafts reaction between electron-rich aromatics and allylic or benzylic alcohols. Moreover, these methods can be applied to the synthesis of natural products. Finally, photoactivation of tosylhydrazones can allow for C–C bond formation when paired with organoboronates. This reaction was probed and the mechanism of photoactivation was elucidated.

Name thesis:degree_name

Doctor of Philosophy

Level thesis:degree_level

Doctoral

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Houston

Year dc:date.issued

2024

Author dc:creator

• Donald, Clayton Paul

Advisor dc:contributor.advisor

• May, Jeremy A

Committee members dc:contributor.committeemember

• Gilbertson, Scott R
• Daugulis, Olafs
• Cuny, Gregory
• Teets, Thomas S

• Synthesis
• Catalysis
• Photoactivation
• Carbon-Carbon Bonds

Language dc:language.iso

en

Handle dc:identifier.uri

https://hdl.handle.net/10657/17741

OAI identifier oai:identifier

oai:uh-ir.tdl.org:10657/17741