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- All Subjects: Organic Chemistry
- All Subjects: bromination
- Creators: Ackerman-Biegasiewicz, Laura
- Creators: Beerman, Eric Christopher
- Member of: Theses and Dissertations
- Status: Published
Targeting Tumors: Inclusion of Functional Groups on Ion-Containing Block Copolymers to Combat Cancer
Despite comprising a variety of bioactive compounds that can be utilized as effective synthetic precursors, the construction of halogenated arenes often relies on hazardous reagents and conditions that pose regioselectivity issues in complex systems. Halodecarboxylation using vanadium-dependent haloperoxidases (VHPOs) has emerged as a sustainable alternative for the synthesis of halogenated arenes. In the Biegasiewicz group, we recently discovered that VHPOs can furnish 3-bromooxindoles from 3-carboxyindoles through a decarboxylation event, followed by oxidation. While this tandem process was exciting, the intermediates of this process, 3- bromoindoles are independently valuable reagents, which necessitated further investigation. Herein we examine the biocatalytic access to bromoindoles for which we addressed the major challenge of undesired oxidation event. The first preventative approach acylated the indole nitrogen, resulting in 1-acetylindole-3-CO2H. This could then be subjected to optimized enzymatic bromination conditions to produce 1-acetyl-3-bromoindole in 98% yield with CiVCPO. The second preventative approach was to modify the reaction conditions, furnishing 1-methyl-3-bromoindole in 73% yield from 1-methylindole-3- CO2H with AmVBPO.
This thesis is about how Fe catalysts can be degraded using photocatalysis and how Fe catalysts can degrade small molecules in conjunction with light. The goal of this paper is to look further into more sustainable methods of organic chemistry. Many current organic chemistry practices involve the use of precious metals. Iron is a more sustainable catalyst because it is abundant and inexpensive which is important for preserving the earth and making the organic chemistry more accessible. Along the same lines, light is a renewable energy source and has demonstrated its ability to aid in reactions. Overall, the goal of this paper is to explore the more sustainable alternatives to harsh and toxic organic chemistry practices through the use of Iron and light.