A5058838222- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Radical Photochemical Reactions
- Crystallography and molecular interactions
- Synthesis and Catalytic Reactions
- Catalytic C–H Functionalization Methods
- Sulfur-Based Synthesis Techniques
- Chemical Synthesis and Analysis
- Synthetic Organic Chemistry Methods
- Biological Activity of Diterpenoids and Biflavonoids
- Click Chemistry and Applications
- Pharmaceutical and Antibiotic Environmental Impacts
- Microbial Natural Products and Biosynthesis
- Advanced Photocatalysis Techniques
- Axial and Atropisomeric Chirality Synthesis
- Advanced Polymer Synthesis and Characterization
- Polymer crystallization and properties
- Asymmetric Synthesis and Catalysis
- Chemistry and Chemical Engineering
- Asymmetric Hydrogenation and Catalysis
- Cyclopropane Reaction Mechanisms
- biodegradable polymer synthesis and properties
University of California, Berkeley
2020-2025
Gilead Sciences (United States)
2025
Allegheny College
2020
Shuffling nitrogen with a light push Manipulation of carbon–nitrogen rings is integral to the synthesis numerous pharmaceutical and agrochemical compounds. Jurczyk et al . report that photoexcitation carbonyl-substituted cyclic amines can shift from inside outside ring framework. The reaction appears proceed through 1,5-hydrogen electronically excited carbonyl, which sets in motion subsequent carbon–carbon bonding rearrangements. Several oxygen sulfur heterocycles were applicable as well....
Under mild blue-light irradiation, α-acylated saturated heterocycles undergo a photomediated one-atom ring contraction that extrudes heteroatom from the cyclic core. However, for nitrogenous heterocycles, this powerful skeletal edit has been limited to substrates bearing electron-withdrawing substituents on nitrogen. Moreover, mechanism and wavelength-dependent efficiency of transformation have remained unclear. In work, we increased electron richness nitrogen in azacycles improve light...
We recently reported a chiral phosphoric acid (CPA) catalyzed enantioselective photomediated ring contraction of piperidines and other saturated heterocycles. By extruding single heteroatom from ring, this transformation builds desirable C(sp3)–C(sp3) bonds in the contracted products; however, origins enantioselectivity remain poorly understood. In work, has been explored across an expanded structurally diverse substrate scope, revealing wide range enantioselectivities (0–99%) using two...
Herein, we report a detailed investigation of the photomediated transformation indazoles to benzimidazoles through nitrogen‐carbon transposition. This phototransposition is known occur in low yield when 1H‐indazoles are subjected high‐energy UVC irradiation. The 2H‐tautomer indazole absorbs light more strongly than 1H‐tautomer at longer wavelengths. We leveraged this improved absorbance profile develop general system for high‐yielding conversion N2‐derivatized (prepared from corresponding...
Saturated cyclic amines (aza-cycles) are ubiquitous structural motifs found in pharmaceuticals, agrochemicals, and bioactive natural products. Given their importance, methods that directly functionalize aza-cycles high demand. Herein, we disclose a fundamentally different approach to functionalizing which relies on C–C cleavage attendant cross-coupling. The initial functionalization step is the generation of underexplored N-fused bicyclo α-hydroxy-β-lactams under mild, visible light...
Herein we report the synthesis of substituted indolizidines and related N-fused bicycles from simple saturated cyclic amines through sequential C-H C-C bond functionalizations. Inspired by Norrish-Yang Type II reaction, functionalization azacycles is achieved forming α-hydroxy-β-lactams precursor α-ketoamide derivatives under mild, visible light conditions. Selective cleavage distal C(sp
Herein, we report a detailed investigation of the photomediated transformation indazoles to benzimidazoles through nitrogen‐carbon transposition. This phototransposition is known occur in low yield when 1H‐indazoles are subjected high‐energy UVC irradiation. The 2H‐tautomer indazole absorbs light more strongly than 1H‐tautomer at longer wavelengths. We leveraged this improved absorbance profile develop general system for high‐yielding conversion N2‐derivatized (prepared from corresponding...
The rearrangement of carbon–carbon (C–C) single bonds in readily available carbocyclic scaffolds can yield uniquely substituted carbocycles that would be challenging to construct otherwise. This is a powerful and often non-intuitive approach for complex molecule synthesis. transition-metal-mediated cleavage C–C has the potential broaden scope this type skeletal remodeling by providing orthogonal selectivities compared more traditional pericyclic carbocation-based rearrangements. To highlight...
The construction of complex aza-cycles is interest to drug discovery due the prevalence nitrogen-containing heterocycles in pharmaceutical agents. Herein we report an intramolecular C-H amination approach afford value-added and complexity-enriched bridged bicyclic amines. Guided by density functional theory nuclear magnetic resonance investigations, determined unique roles light heat activation bicyclization mechanism. We applied both a synergistic fashion, achieving gram-scale aza-cycle synthesis.