A5029266326- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Catalytic C–H Functionalization Methods
- Chemical Synthesis and Reactions
- Chemical Reactions and Mechanisms
- Energetic Materials and Combustion
- Synthesis and Catalytic Reactions
- Chemical Reactions and Isotopes
- Radical Photochemical Reactions
- Asymmetric Hydrogenation and Catalysis
- Synthetic Organic Chemistry Methods
- Thermal and Kinetic Analysis
- Chemical Reaction Mechanisms
- Crystallography and molecular interactions
- Organoboron and organosilicon chemistry
- Asymmetric Synthesis and Catalysis
- Cyclopropane Reaction Mechanisms
- Inorganic and Organometallic Chemistry
- Chemical Synthesis and Analysis
- Catalytic Cross-Coupling Reactions
- Fluorine in Organic Chemistry
- Carbon dioxide utilization in catalysis
- Analytical chemistry methods development
University of California, Berkeley
2018-2025
University of California System
2025
University of California, Riverside
2021-2022
Deconstructive functionalizations involving scission of carbon-carbon double bonds are well established. In contrast, unstrained C(sp3)-C(sp3) bond cleavage and functionalization have less precedent. Here we report the use deconstructive fluorination to access mono- difluorinated amine derivatives by in saturated nitrogen heterocycles such as piperidines pyrrolidines. Silver-mediated ring-opening using Selectfluor highlights a strategy for cyclic late-stage skeletal diversification,...
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...
The chemical synthesis of medium (8-11 membered) and large sized (≥12 cyclic systems is often challenging. introduction transannular strain loss degrees freedom in forming macrocycles result poor reaction kinetics thermodynamics (i.e., thermodynamically disfavored at equilibrium). To address these challenges, we herein report a strategy for the medium-to-large rings, which leverages strain-release metal templating through palladium-mediated C-C cleavage/cross-coupling. By means DOSY NMR...
The photoexcited nitroarene mediated oxidative cleavage of methoximes is presented. utility the reaction shown in a broad substrate scope and its relevance underlined several complex late-stage examples.
Given its relevance across numerous fields, reductive amination is one of the oldest and most widely used methods for amine synthesis. As a cornerstone synthetic chemistry, it has largely remained unchanged since discovery over century ago. Herein, we report mechanistically driven development complementary reaction, which reductively aminates C-C σ-bond carbonyls, not carbonyl C-O π-bond, generating value-added linear cyclic 3° amines in modular fashion. Critical to our success were...
Dual Brønsted/Lewis acid catalysis involving environmentally benign, readily accessible protic and iron promotes site-selective
3,3-Dinitratooxetane was prepared by the addition of dinitrogen pentoxide to oxetan-3-one and a crystal structure obtained. Hot plate test 3,3-dinitratooxetane (<bold>1</bold>).
Despite the variety of energetic polyoxetane binders, oxirane-based glycidyl azide polymer (GAP) has largely succeeded in market due to its advantageous properties. Nevertheless, it suffers from various drawbacks such as non-uniform chain termination, possible chlorine content (flame retardant), and toxic epichlorohydrin required for synthesis. These problems can be bypassed using structurally related poly(3-azidooxetane). Unfortunately, is only accessible moderate yield by polymerization...
3-(Nitromethylene)oxetane was identified as a promising scaffold for the straightforward synthesis of energetic oxetane monomers via conjugate addition. The use tetrazoles provided compounds with exciting properties superior to prior art.
Dual Brønsted/Lewis acid catalysis involving environmentally benign, readily accessible protic and iron promotes site-selective tert-butylation of electron-rich arenes using di-tert-butylperoxide. This transformation inspired the development a synergistic catalyzed aromatic alkylation that fills gap in Friedel–Crafts reaction literature by employing unactivated tertiary alcohols as alkylating agents, leading to new quaternary carbon centers. Corroborated DFT calculations, Lewis serves role...
Methoximes are a versatile directing group for variety of C–H functionalizations. Despite their importance as powerful functional handle, conversion to the parent ketone, which is often desired, usually requires harsh and intolerant reaction conditions that make application in late-stage context problematic. Here, we present an alternative set achieve mild tolerant methoximes ketones using photoexcited nitroarenes. The utility this methodology showcased its total synthesis cephanolide D....