Researcher ORCID Identifier
0009-0005-5781-2266
Graduation Year
2025
Date of Submission
12-2024
Document Type
Open Access Senior Thesis
Degree Name
Bachelor of Arts
Department
Biochemistry
Reader 1
Anna G. Wenzel
Reader 2
Sadie C. Otte
Terms of Use & License Information
Abstract
Amines are a powerful functional group bearing great significance in daily life, with upwards of 40% of pharmaceutical products and 20% of agrochemicals possessing chiral amines. The hydroamination of olefins is one of several methods that generate an amine from an organic source, directly adding nitrogen across a carbon-carbon pi bond with complete atom economy. Traditional methods of hydroamination are challenged by the use of expensive transition metal catalysts facing limited supply. We herein report a silver-catalyzed, intermolecular Markovnikov hydroamination of styrene using benzyl carbamate as the nitrogen source. This methodology has proven to offer a more sustainable and economically practical alternative to traditional catalytic routes. The reaction exhibits stellar regioselectivity, providing the desired product in moderate to good yields. Preliminary mechanistic studies suggest that the reaction proceeds via the formation of a nitrogen radical and undergoes enhanced conversion in the presence of mild, inexpensive oxidants.
Recommended Citation
Schmidt, Andrew, "Discovery of Silver-Catalyzed Intermolecular Markovnikov Hydroamination of Olefins" (2025). CMC Senior Theses. 3843.
https://scholarship.claremont.edu/cmc_theses/3843
Included in
Biochemistry Commons, Medicinal-Pharmaceutical Chemistry Commons, Organic Chemistry Commons