A5074608135- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Catalytic C–H Functionalization Methods
- Catalytic Cross-Coupling Reactions
- Asymmetric Hydrogenation and Catalysis
- Crystallography and molecular interactions
- Cyclopropane Reaction Mechanisms
- Organometallic Complex Synthesis and Catalysis
- Synthetic Organic Chemistry Methods
- Catalytic Alkyne Reactions
- Chemical Synthesis and Analysis
- Fluorine in Organic Chemistry
- Corporate Taxation and Avoidance
- Electrocatalysts for Energy Conversion
- Organoboron and organosilicon chemistry
- Asymmetric Synthesis and Catalysis
- Adenosine and Purinergic Signaling
- Fuel Cells and Related Materials
- Receptor Mechanisms and Signaling
- Catalysis and Oxidation Reactions
- Radical Photochemical Reactions
- Advanced battery technologies research
- Sulfur-Based Synthesis Techniques
- Synthesis and Catalytic Reactions
- CO2 Reduction Techniques and Catalysts
ETH Zurich
2024-2025
Scripps Research Institute
2018-2024
Northeastern University
2014-2021
University of Tsukuba
2018-2019
Okinawa Institute of Science and Technology Graduate University
2018
Universidad del Noreste
2017
Abstract A nickel‐catalyzed conjunctive cross‐coupling of alkenyl carboxylic acids, aryl iodides, and aryl/alkenyl boronic esters is reported. The reaction delivers the desired 1,2‐diarylated 1,2‐arylalkenylated products with excellent regiocontrol. To demonstrate synthetic utility method, a representative product prepared on gram scale then diversified to eight 1,2,3‐trifunctionalized building blocks using two‐electron one‐electron logic. Using this three routes toward bioactive molecules...
A tungsten-catalyzed hydroboration of unactivated alkenes at distal C(sp
A catalytic γ-selective <italic>syn</italic>-hydroarylation of alkenyl carbonyl compounds using arylboronic acids has been developed a substrate directivity approach with palladium(<sc>ii</sc>) catalyst.
A flurry of recent research has centered on harnessing the power nickel catalysis in organic synthesis. These efforts have been bolstered by contemporaneous development well-defined (pre)catalysts with diverse structure and reactivity. In this report, we present ten different bench-stable, 18-electron, formally zero-valent nickel-olefin complexes that are competent pre-catalysts various reactions. Our investigation includes preparations novel, bench-stable Ni(COD)(L)...
Abstract A nickel‐catalyzed conjunctive cross‐coupling of alkenyl carboxylic acids, aryl iodides, and aryl/alkenyl boronic esters is reported. The reaction delivers the desired 1,2‐diarylated 1,2‐arylalkenylated products with excellent regiocontrol. To demonstrate synthetic utility method, a representative product prepared on gram scale then diversified to eight 1,2,3‐trifunctionalized building blocks using two‐electron one‐electron logic. Using this three routes toward bioactive molecules...
Metathesis and reversible catalytic reactions are fundamentally intriguing powerful tools in modern synthetic chemistry. While most predicated on breaking forming reactive functional groups, the ability to leverage C–H bond as a group into metathesis has proved be exceptionally challenging. Here, we develop C–H/C–X reaction through radical swapping protocol where hydrogen halogen traded between molecules via atom transfer (HAT) (XAT) that allows for mild halogenation. The reversibility of...
Viable anionic exchange membrane (AEM) electrolysis for H 2 production requires highly active hydrogen evolution reaction (HER) catalysts that are also robust and cost-effective. Traditionally juxtaposition of two transition metals with one being more oxophilic is necessary easier access to water in the inner Helmholtz plane as a source protons crucial Volmer step enhanced HER activity. However, they prone passivation at anodic potentials or deactivation via formation sub-surface metal...
We report a one-step, Ru(II)-catalyzed cyclopropanation reaction that is conceptually different from the previously reported protocols include Corey–Chaykovsky, Simmons–Smith, and metal-catalyzed carbene attack on olefins. Under current protocol, various alcohols esters are transformed into sulfone substituted cyclopropanes with excellent isolated yields diastereoselectivities. This new forms highly congested cyclopropane products three C–C bonds, or two chiral centers one quaternary carbon...
Antagonism of the adenosine <mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" id="M1"><mml:mrow><mml:msub><mml:mrow><mml:mi mathvariant="normal">A</mml:mi></mml:mrow><mml:mrow><mml:mn mathvariant="normal">2</mml:mn><mml:mi mathvariant="normal">A</mml:mi></mml:mrow></mml:msub></mml:mrow></mml:math> receptor on T cells blocks hypoxia-adenosinergic pathway to promote tumor rejection. Using an in vivo immunoassay based Concanavalin A mouse model, a series...
Hydrogen atom transfer (HAT) from a metal-hydride is reliable and powerful method for functionalizing unsaturated C–C bonds in organic synthesis. Cobalt hydrides (Co–H) have garnered significant attention this field, where the weak Co–H are most commonly generated catalytic fashion through mixture of stoichiometric amounts peroxide oxidant silane reductant. Here we show that reverse process HAT to an alkene, i.e. hydrogen abstraction C–H adjacent radical, can be leveraged generate...
Hydrogen atom transfer (HAT) from a metal-hydride is reliable and powerful method for functionalizing unsaturated C-C bonds in organic synthesis. Cobalt hydrides (Co-H) have garnered significant attention this field, where the weak Co-H are most commonly generated catalytic fashion through mixture of stoichiometric amounts peroxide oxidant silane reductant. Here we show that reverse process HAT to an alkene, i.e. hydrogen abstraction C-H adjacent radical, can be leveraged generate...
Abstract 3‐(Trifluoromethyl)indoles were successfully synthesized by cyclization through intramolecular oxidative C−H/N−H coupling of α‐(trifluoromethyl)styrenes bearing a sulfonamido group at the ortho‐ position. On treatment with cerium (IV) ammonium nitrate (CAN) in tert ‐butyl alcohol, o ‐sulfonamido‐α‐(trifluoromethyl)styrenes underwent assisted microwave irradiation to afford corresponding 3‐trifluoromethylated indoles. By using this method, 3‐(trifluoromethyl)indoles various...
A flurry of recent research has centered on harnessing the power nickel catalysis in organic synthesis. These efforts have been bolstered by contemporaneous synthesis, characterization, and optimization well-defined (pre)catalysts with diverse structure reactivity. In this report, we present development ten different bench-stable, 18-electron, formally zero-valent nickel–olefin complexes that are shown to be competent pre-catalysts various reactions. Our investigation includes preparations...
A unique family of N,N,π,C-palladacycles are synthesized from 8-aminoquinoline-coupled nopol derivatives through directed 1,2-migratory insertion in situ generated arylpalladium(II) species followed by β-carbon elimination. These palladacycles have exceptional stability under air and moisture at room temperature, enabling successful isolation characterization X-ray crystallography, NMR, high-resolution mass spectrometry. Computational studies shed light on the facile β-alkyl elimination step...
Achieving regio- and stereoselective formation of products from simple chemical building blocks is one the most important roles catalysis in organic synthesis. Repositioning an alkene functional group through catalytic isomerization represents a powerful synthetic strategy for preparing valuable comparatively feedstocks. The utility this approach, however, hinges on ability to control positional stereoisomerism access single product among numerous potential isomeric byproducts. Here,...
A tungsten-catalyzed hydroboration of unactivated alkenes at distal C(sp3)–H bonds aided by native directing groups is described herein. The method characterized its simplicity, exquisite regio- and chemoselectivity wide substrate scope, offering a complementary site-selectivity pattern to other metal-catalyzed borylation reactions chain-walking protocols.
Tungsten catalysis has played an instrumental role in the history of organometallic chemistry, with electrophilic, fully oxidized W(VI) catalysts featuring prominently olefin polymerization and metathesis reactions. Here, we report that simple W(0) precatalyst, W(CO)<sub>6</sub>, catalyzes isomerization hydrocarbonylation alkenes via a W(0)/W(II) redox couple. The 6- to 7-coordinate geometry changes associated this process are key allowing take place over multiple positions stop...
A stereodivergent, W-catalyzed alkene isomerization is reported, leading to either E - or Z -β,γ-unsaturated carbonyl compounds based on the ligand environment around metal.
We report a one-step, Ru(II)-catalyzed cyclopropanation reaction that is conceptually different from the previously reported protocols include Corey-Chaykovsky, Simmons-Smith, and metal catalyzed carbene attack on olefins. Under current protocol, various alcohols are transformed into sulfone substituted cyclopropanes with excellent isolated yields diastereoselectivities. This new forms highly congested cyclopropane products three C–C bonds, or two chiral centers one quaternary carbon center....
Anion-exchange membranes (AEMs) provide an attractive alternative future for fuel cells as well electrolyzers (i.e.,hydrogen production). To gain higher efficiency reduce costs in electrochemical water splitting, NUCRET has successfully developed high performance non-PGM catalysts hydrogen evolution reaction (HER) and oxygen (OER) that are compatible AEM solid polymer electrolytes (specifically, A-201, Tokuyama, Japan). These 60% Ni-Cr/C HER 40% Ni-Fe/Raney-PANI OER. Figure 1 shows the...