Date of Award
Spring 2024
Document Type
Dissertation
Degree Name
Doctor of Philosophy (PhD)
Department
Chemistry
First Advisor
Ellman, Jonathan
Abstract
Functionalization of imine C−H bonds allows for rapid and modular synthesis of nitrogen heterocycles which are present in nearly two-thirds of U.S. FDA approved drugs. The first chapter describes work on the synthesis of a class of nitrogen heterocycles by a new type of reaction, imidoyl C−H carbamylation. Unconventional chiral sulfur(VI) compounds, such as sulfoximines are also increasingly relevant to drug and agrochemical discovery. The second chapter details a catalytic enantioselective sulfur-alkylation of N-acylsulfenamides to access enantioenriched sulfilimine intermediates en route to sulfoximines. The third and fourth chapters demonstrate further methods to access sulfilimines by way of sulfur-arylation with commercially abundant boronic acid and aryl iodide inputs, respectively. Finally, the fifth chapter describes orthogonal methods to access N-acylsulfenamide starting inputs from abundant and diverse commercial materials through a sulfur-functionalization and elimination strategy.
Recommended Citation
Greenwood, Nathaniel Scott, "Rhodium(III)-Catalyzed Heterocycle Synthesis and New Approaches to High Oxidation State Sulfur Pharmacophores by Sulfur-Functionalization of Sulfenamides" (2024). Yale Graduate School of Arts and Sciences Dissertations. 1265.
https://elischolar.library.yale.edu/gsas_dissertations/1265