A5002525234- Radical Photochemical Reactions
- Catalytic C–H Functionalization Methods
- Catalytic Cross-Coupling Reactions
- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Plant biochemistry and biosynthesis
- CO2 Reduction Techniques and Catalysts
- Sulfur-Based Synthesis Techniques
- Chemical Synthesis and Analysis
- Oxidative Organic Chemistry Reactions
- Asymmetric Synthesis and Catalysis
- Microbial Natural Products and Biosynthesis
- Synthesis and Catalytic Reactions
- Asymmetric Hydrogenation and Catalysis
- Click Chemistry and Applications
- Advanced Synthetic Organic Chemistry
- Synthesis and Characterization of Heterocyclic Compounds
- Vanadium and Halogenation Chemistry
- Virus-based gene therapy research
- Nanomaterials for catalytic reactions
- Synthesis of β-Lactam Compounds
- Electrocatalysts for Energy Conversion
- Protein Degradation and Inhibitors
- Synthetic Organic Chemistry Methods
- Organoboron and organosilicon chemistry
Bristol-Myers Squibb (Germany)
2023-2025
Bristol-Myers Squibb (United States)
2023-2025
Scripps Institution of Oceanography
2019-2024
Scripps Research Institute
2021-2024
Scripps (United States)
2019-2024
Torrey Pines Institute For Molecular Studies
2019-2024
Merck & Co., Inc., Rahway, NJ, USA (United States)
2022
Boston College
2018
Eli Lilly (United States)
2017
The synthesis of terpenes is a large field research that woven deeply into the history chemistry. Terpene biosynthesis case study how logic modular design can lead to diverse structures with unparalleled efficiency. This work leverages modern nickel-catalyzed electrochemical sp2-sp3 decarboxylative coupling reactions, enabled by silver nanoparticle-modified electrodes, intuitively assemble terpene natural products and complex polyenes using simple building blocks. step change in efficiency...
A useful protocol for achieving decarboxylative cross-coupling (DCC) of redox-active esters (RAE, isolated or generated in situ) and halo(hetero)arenes is reported. This pragmatically focused study employs a unique Ag-Ni electrocatalytic platform to overcome numerous limitations that have plagued this strategically powerful transformation. In its optimized form, coupling partners can be combined surprisingly simple way: open the air, using technical-grade solvents, an inexpensive ligand Ni...
Carboxylic acids, the most versatile and ubiquitous diversity input used in medicinal chemistry for canonical polar bond constructions such as amide synthesis, can now be employed a fundamentally different category of reaction to make C-C bonds by harnessing power radicals. This outlook serves user-guide aid practitioners both design syntheses that leverage simplifying this disconnection precise tactics enable them. Taken together, emerging area holds potential rapidly accelerate access...
ConspectusTransition-metal catalyzed cross-coupling reactions are fundamental in organic chemistry, facilitating strategic bond formations for accessing natural products, materials, agrochemicals, and pharmaceuticals. Redox chemistry enables access to elusive mechanisms through single-electron processes as an alternative classical two-electron strategies predominated by palladium catalysis. The seminal reports of Baran, MacMillan, Doyle, Molander, Weix, Lin, Fu, Reisman, others merging redox...
Abstract There is a pressing need, particularly in the field of drug discovery, for general methods that will enable direct coupling tertiary alkyl fragments to (hetero)aryl halides. Herein uniquely powerful and simple set conditions achieving this transformation with unparalleled generality chemoselectivity disclosed. This new protocol placed context other recently reported methods, applied simplify routes known bioactive building blocks molecules, scaled up both batch flow. The role...
The direct, stereospecific amination of alkylboronic and borinic esters can be conducted by treatment the organoboron compound with methoxyamine potassium tert-butoxide. In addition to being stereospecific, this process also enables direct tertiary boronic in an efficient fashion.
A simple protocol is outlined herein for rapid access to enantiopure unnatural amino acids (UAAs) from trivial glutamate and aspartate precursors. The method relies on Ag/Ni-electrocatalytic decarboxylative coupling can be rapidly conducted in parallel (24 reactions at a time) ascertain viability followed by scale-up the generation of useful quantities UAAs exploratory studies.
Pd(COD)(DQ) (COD=1,5-cyclooctadiene, DQ=duroquinone) is a robust, air-stable, and well-defined 18-electron Pd(0)–olefin complex first synthesized by Sakai et al. in 1983. Herein, we describe an operationally convenient synthetic procedure to prepare this on decagram scale; show that it undergoes facile ligand exchange with phosphines, N-heterocyclic carbenes, other catalytically important ancillary ligands give stable organometallic products; demonstrate its catalytic competence numerous...
Disclosed herein is the invention of a method for facile C–H alkylation range (hetero)arenes under Ni-catalysis. This reaction takes place at 50 °C, scalable, tolerates heterocyclic substrates, and can be applied to both primary complex secondary alkyl donors. Success hinges on use sulfonylhydrazide-based donors that mildly generate radicals thereby obviating need halide precursors require more harsh conditions activate. The demonstrated substrate scope broad (>70 examples), was also...
Abstract There is a pressing need, particularly in the field of drug discovery, for general methods that will enable direct coupling tertiary alkyl fragments to (hetero)aryl halides. Herein uniquely powerful and simple set conditions achieving this transformation with unparalleled generality chemoselectivity disclosed. This new protocol placed context other recently reported methods, applied simplify routes known bioactive building blocks molecules, scaled up both batch flow. The role...
There is an urgent need, particularly in the field of drug discovery, for general methods that will enable direct coupling tertiary alkyl fragments to (hetero)aryl halides. This early disclosure serves this purpose by informing community a uniquely powerful and simple set conditions achieving transformation with unparalleled generality chemoselectivity.
A method for deoxyfluorination of aliphatic primary, secondary, and tertiary alcohols is reported, employing a nontrigonal phosphorus triamide base-free alcohol activation in conjunction with an organic soluble fluoride donor triarylborane shuttling catalyst. Mechanistic experiments are consistent reaction that proceeds by the collapse oxyphosphonium fluoroborate ion pair transfer. The substrate scope complements existing methods enables preparation homochiral secondary alkylfluorides...
A simple protocol is outlined herein for rapid access to enantiopure unnatural amino acids from trivial glutamate and aspartate precursors. The method relies on Ag/Ni-electrocatalytic decarboxylative coupling can be rapidly conducted in parallel (24 reactions at a time) ascertain viability followed by scale-up the generation of useful quantities UAAs exploratory studies.
A simple protocol for the direct Buchwald-Hartwig cross-coupling of (hetero)aryl halides with unprotected aminoglutarimide to afford diverse Cereblon Binding Motifs is disclosed. This C-N method development was enabled by high throughput combinatory screening key reaction parameters namely solvents, temperatures and ligands. Scope studies revealed generality across various heteroaryl aryl halides, proceeding under mild conditions. In comparison, this demonstrated strategic superiority over...
We describe a two-step process for the synthesis of substituted bicyclo[1.1.0]butanes. A photo-Hunsdiecker reaction generates iodo-bicyclo[1.1.1]pentanes under metal-free conditions at room temperature. These intermediates react with nitrogen and sulfur nucleophiles to afford bicyclo[1.1.0]butane products.
Acyl azetidines exhibit nonplanar hybridization, leading to lower amide-like character of the corresponding (O)C–N bonds. This impacts N-acryloyl by producing enhanced electrophilicy at appended Michael acceptors. Herein, reactivity data are reported in presence glutathione (GSH) phosphate buffer (pH 7.4) 37 °C. Wide ranges observed varying substitution acceptor or modulating electron-withdrawing substituents C3 position azetidine.
A simple protocol for the Buchwald–Hartwig cross-coupling of (hetero)aryl halides with unprotected aminoglutarimide to afford diverse cereblon binding motifs is disclosed. The development this C–N method was enabled by high-throughput combinatory screening solvents, bases, temperatures, and ligands. Scope studies revealed generality across various heteroaryl aryl reaction proceeding under mild conditions. In comparison, demonstrated strategic superiority over previously reported approaches,...
Transition-metal cata-lyzed cross-coupling reactions are fundamental in organic chemistry, facilitating strategic bond formations for accessing natural products, mate-rials, agrochemicals, and pharmaceuticals. Redox chemistry enables access to elusive mechanisms through single-electron processes as an alternative classical two-electron strategies, which predominated by palladium catalysis. The hallmark of this redox platform is the systematic modulation transition-metal oxidation states a...
Carboxylic acids, the most versatile and ubiquitous diversity input used in medicinal chemistry for canonical polar bond constructions such as amide synthesis, can now be employed a fundamentally different category of reaction to make C–C bonds by harnessing power radicals. This outlook serves user guide aid practitioners both design syntheses that leverage simplifying this disconnection precise tactics enable them. Taken together emerging area holds potential rapidly accelerate access
The polar retrosynthetic analysis has been widely employed in the field of organic synthesis and forms basis undergraduate curriculum. Although most reactions rely on this rubric to guide their strategic application, implementation often requires a long list ancillary considerations mitigate chemoselectivity oxidation state issues involving protecting groups precise reaction choreography. Here we demonstrate complete departure from norm by use radical based Ni/Ag-electrocatalytic cross...
A useful protocol for achieving decarboxylative cross coupling (DCC) of redox-active esters (RAE, isolated or generated in situ) and halo(hetero)arenes is reported. This pragmatically focused study employs a unique Ag-Ni electrocatalytic platform to overcome numerous limitations that have plagued this strategically powerful transformation. In its optimized form partners can be combined surprisingly simple way: open the air, technical grade solvents, an inexpensive ligand Ni source,...