A5002569198- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Fluorine in Organic Chemistry
- Inorganic Fluorides and Related Compounds
- Radical Photochemical Reactions
- Catalytic C–H Functionalization Methods
- Chemical Reactions and Mechanisms
- Cyclization and Aryne Chemistry
- Synthetic Organic Chemistry Methods
- Cyclopropane Reaction Mechanisms
- Chemical Reaction Mechanisms
- Asymmetric Synthesis and Catalysis
- Asymmetric Hydrogenation and Catalysis
- Monoclonal and Polyclonal Antibodies Research
- Click Chemistry and Applications
- Peptidase Inhibition and Analysis
Merck & Co., Inc., Rahway, NJ, USA (United States)
2023
Princeton University
2018-2020
Yale University
2014-2016
Herein, we report a convenient and broadly applicable strategy for the difluoromethylation of aryl bromides by metallaphotoredox catalysis. Bromodifluoromethane, simple commercially available alkyl halide, is harnessed as an effective source difluoromethyl radical silyl-radical-mediated halogen abstraction. The merger this fluoroalkyl electrophile activation pathway with dual nickel/photoredox catalytic platform enables diverse array heteroaryl under mild conditions. utility procedure...
The asymmetric borylation of N-tert-butanesulfinyl imines with bis(pinacolato)diboron is achieved using a Cu(II) catalyst and provides access to synthetically useful pharmaceutically relevant α-amino boronic acid derivatives. Cu(II)-catalyzed reaction performed on the benchtop in air at room temperature commercially available, inexpensive reagents low loadings. A variety imines, including ketimines, react readily provide α-sulfinamido boronate esters good yields high stereoselectivity. In...
New biocompatible methods for post-translational protein modification are challenging to develop but crucial create improved chemical probes and optimize next-generation biologic therapies such as antibody–drug conjugates (ADCs). Herein, we describe the bottom-up construction of an aqueous nickel-catalyzed cross-coupling chemospecific arylation cysteine residues on peptides proteins its use preparation ADCs. A variety arene linkages exemplified, enabling incorporation small molecules,...
Abstract Herein, we report a convenient and broadly applicable strategy for the difluoromethylation of aryl bromides by metallaphotoredox catalysis. Bromodifluoromethane, simple commercially available alkyl halide, is harnessed as an effective source difluoromethyl radical silyl‐radical‐mediated halogen abstraction. The merger this fluoroalkyl electrophile activation pathway with dual nickel/photoredox catalytic platform enables diverse array heteroaryl under mild conditions. utility...
Multisubstituted tropanes and indolizidines have been prepared with high regio- stereoselectivity by the [3+2] cycloaddition of unstabilized azomethine ylides generated from readily trimethylsilyl-substituted 1,2-dihydropyridines via protonation or alkylation followed desilylation. Starting bearing a ring trimethylsilyl substituent at 6-position, an intermolecular alkylation/desilylation provides endocyclic that successfully undergo range symmetrical unsymmetrical alkyne alkene...
A cascade benzyne Fries rearrangement is reported that offers facile access to 2,3-disubstituted phenols, allowing for two points of diversity on the adduct. The methodology utilizes an <i>o</i>-(trimethylsilyl)triflate phenol as a common intermediate, from which substitution phenolic oxygen readily yields precursors undergo requisite in presence amine nucleophile, base, and fluoride source.
Correction to: A Novel Cascade Benzyne Nucleophilic Addition/Fries Rearrangement for Entry into 2,3-Disubstituted PhenolsSynlett eFirstDOI: 10.1055/s-0036-1588938
Abstract The enantioselective synthesis of the title compounds from aldimines uses a low catalyst loading.