A5026401077- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Synthesis and Properties of Aromatic Compounds
- Catalytic C–H Functionalization Methods
- Radical Photochemical Reactions
- Fluorine in Organic Chemistry
- Organic Chemistry Cycloaddition Reactions
- Fullerene Chemistry and Applications
- Cyclization and Aryne Chemistry
- Oxidative Organic Chemistry Reactions
- Synthetic Organic Chemistry Methods
- Crystallography and molecular interactions
- Axial and Atropisomeric Chirality Synthesis
- Conducting polymers and applications
- Organoboron and organosilicon chemistry
- Organic Electronics and Photovoltaics
- Inorganic Fluorides and Related Compounds
- Algebraic and Geometric Analysis
- Electrochemical sensors and biosensors
- Chemical Reaction Mechanisms
- Porphyrin and Phthalocyanine Chemistry
- Analytical Chemistry and Sensors
- Supramolecular Self-Assembly in Materials
- Spectral Theory in Mathematical Physics
- Catalytic Alkyne Reactions
Massachusetts Institute of Technology
2025
Princeton University
2018-2022
University of California, Berkeley
2017
University of California, Los Angeles
2015-2017
Transition metal-catalyzed arene functionalization has been widely used for molecular synthesis over the past century. In this arena, copper catalysis long considered a privileged platform due to propensity of high-valent undergo reductive elimination with wide variety coupling fragments. However, sluggish nature oxidative addition limited copper's capacity broadly facilitate haloarene protocols. Here, we demonstrate that problem can be overcome an aryl radical-capture mechanism, wherein...
The development of palladium-catalyzed cross-coupling methods for the activation C(sp2)-Br bonds facilitated access to arene-rich molecules, enabling a concomitant increase in prevalence this structural motif drug molecules recent decades. Today, there is growing appreciation value incorporating saturated C(sp3)-rich scaffolds into pharmaceutically active as means achieve improved solubility and physiological stability, providing impetus develop new coupling strategies these challenging...
Aryl halides are a fundamental motif in synthetic chemistry, playing critical role metal-mediated cross-coupling reactions and serving as important scaffolds drug discovery. Although thermal decarboxylative functionalization of aryl carboxylic acids has been extensively explored, the scope existing halodecarboxylation methods remains limited, there currently exists no unified strategy that provides access to any type halide from an acid precursor. Herein, we report general catalytic method...
We report a copper-catalyzed strategy for arylboronic ester synthesis that exploits photoinduced ligand-to-metal charge transfer (LMCT) to convert (hetero)aryl acids into aryl radicals amenable ambient-temperature borylation. This near-UV process occurs under mild conditions, requires no prefunctionalization of the native acid, and operates broadly across diverse aryl, heteroaryl, pharmaceutical substrates. also one-pot procedure decarboxylative cross-coupling merges catalytic LMCT...
Trifluoromethylation via broken C-F bonds Trifluoromethyl substituents are widely used in pharmaceutical research to tune the properties of drug candidates. Generally, they introduced intact through formation carbon-carbon bonds. Levin et al. discovered an unusual alternative mechanism, which borane abstracts fluoride from CF 3 group a gold complex. The activated 2 fragment can then bond wide variety other carbon added same center. Return liberates trifluoromethylated compound metal. This...
The mechanisms and selectivities of the cycloadditions tropone to dimethylfulvene have been investigated with M06-2X B3LYP-D3 density functional theory (DFT) calculations quasi-classical direct molecular dynamics simulations. originally proposed reaction mechanism (Houk) involves a highly peri-, regio-, stereoselective [6F + 4T] cycloaddition [4π] [6π], followed by [1,5] hydrogen shift, and, finally, second [6 4] [6π] cyclopentadiene moiety [4π]. Paddon-Row Warrener an alternative mechanism:...
Abstract Here, we demonstrate that a metallaphotoredox‐catalyzed cross‐electrophile coupling mechanism provides unified method for the α‐arylation of diverse activated alkyl chlorides, including α‐chloroketones, α‐chloroesters, α‐chloroamides, α‐chlorocarboxylic acids, and benzylic chlorides. This strategy, which is effective wide variety aryl bromide partners, predicated upon halogen atom abstraction/nickel radical‐capture generically successful across an extensive range carbonyl...
Polypyrrole is functionalized by deprotonation of its oxidized state, followed a thiol-Michael addition reaction. It found that this process produced emissive compositions. This feature to be diagnostic the functionalization and relative solvation water, wherein enhanced interactions with solvent gave higher emission intensities. The thiol-conjugation method shown general can extended range polar, nonpolar, aromatic materials. Thiol-conjugated materials retain electroactivity characteristic...
Abstract Here, we demonstrate that a metallaphotoredox‐catalyzed cross‐electrophile coupling mechanism provides unified method for the α‐arylation of diverse activated alkyl chlorides, including α‐chloroketones, α‐chloroesters, α‐chloroamides, α‐chlorocarboxylic acids, and benzylic chlorides. This strategy, which is effective wide variety aryl bromide partners, predicated upon halogen atom abstraction/nickel radical‐capture generically successful across an extensive range carbonyl...
Density functional theory calculations were performed on a set of 13 transannular Diels-Alder (TADA) reactions with 10-18-membered rings. The results compared those for bimolecular and intramolecular in order to investigate the controlling factors high TADA reactivities. effects tether length, heteroatoms, alkynyl dienophiles reactivity analyzed. We found correlation between length reactivity, specifically 12-membered macrocycles undergoing cycloaddition most readily. Furthermore, modifying...
Aryl carboxylic acids are valuable, stable, and abundant functional handles in organic synthesis. Historically, their activation with established two-electron methods requires forcing conditions, such protocols limited scope. In contrast, we envisioned that copper’s ability to generate open-shell species through ligand-to-metal charge transfer (LMCT), combined its unique capacity act as a potential aroyloxy aryl radical reservoir, could mediate facile light- copper-enabled aromatic...
Key words helical structures - cyclization polycyclic aromatic hydrocarbons
Key words polycyclic aromatic hydrocarbons - ring-closing metathesis fluorescence
Key words fullerenes - Diels–Alder cycloaddition inverse electron demand
Key words polycyclic aromatic hydrocarbons - strained structures circular dichroism