2018 Theses Doctoral
Novel Methodologies for the Photochemical and Photocatalytic Generation of Nitrogen-Containing Pharmacophores
Photochemical transformations give rise to radical intermediates that are enabling tools for constructing molecular scaffolds in alternative methods from traditional two-electron processes. Herein, we detail four discrete projects focused on harnessing photochemically-created radicals for building nitrogen-containing architectures. We first explored a formal [5+2] photochemical cycloaddition of vinyl-pyrrolidinones in order to efficiently reach densely functionalized azepane motifs from simple aldehydes and pyrrolidinones. Second, we describe the discovery and development of a cobalt and photoredox catalyzed hydroaminoalkylation of conjugated dienes to afford functionalized homoallylic amines. Third, we explored the union of metal-nitrene catalysts and photoredox in efforts to forge new aliphatic C-N bonds. Finally, we established a method for the remote functionalization of unactivated sp3 C-H bonds with nickel metallophotoredox, which can be specifically controlled to deliver a new C-C bond at different unactivated methylenes.
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More About This Work
- Academic Units
- Chemistry
- Thesis Advisors
- Rovis, Tomislav
- Degree
- Ph.D., Columbia University
- Published Here
- July 21, 2018