Photoredox activation of carbon dioxide and unactivated aliphatic carbonyl compounds

Chapter 1: Photoredox Activation of Carbon Dioxide for Amino Acid Synthesis in Continuous Flow. Although carbon dioxide (CO₂ ) is highly abundant, its low reactivity has limited its use in chemical synthesis. In particular, methods for carbon-carbon bond formation generally rely on two-electron mechanisms for CO₂ activation and require highly activated reaction partners. Alternatively, radical pathways accessed via photoredox catalysis could provide new reactivity under milder conditions. Here we demonstrate the direct coupling of CO₂ and amines via the single-electron reduction of CO₂ for the photoredox-catalyzed continuous flow synthesis of [alpha]amino acids. By leveraging the advantages of utilizing gases and photochemistry in flow, a commercially available organic photoredox catalyst effects the selective [alpha]-carboxylation of amines that bear various functional groups and heterocycles.

Name thesis:degree_name

Doctoral

Department dc:contributor.department

Massachusetts Institute of Technology. Department of Chemistry

Grantor dc:publisher

Massachusetts Institute of Technology

Year dc:date.issued

2019

Author dc:creator

• Seo, Hyowon,Ph. D.Massachusetts Institute of Technology.

Advisor dc:contributor.advisor

• Timothy F. Jamison.

• Chemistry.

Statement dc:rights

• MIT theses are protected by copyright. They may be viewed, downloaded, or printed from this source but further reproduction or distribution in any format is prohibited without written permission.

Licence dc:rights.uri

• http://dspace.mit.edu/handle/1721.1/7582

Language dc:language.iso

eng

Handle dc:identifier.uri

https://hdl.handle.net/1721.1/124052

OAI identifier oai:identifier

oai:dspace.mit.edu:1721.1/124052