A5084066280- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Radical Photochemical Reactions
- Catalytic C–H Functionalization Methods
- Catalytic Cross-Coupling Reactions
- Sulfur-Based Synthesis Techniques
- Asymmetric Synthesis and Catalysis
- Oxidative Organic Chemistry Reactions
- Synthetic Organic Chemistry Methods
- Organoboron and organosilicon chemistry
- Asymmetric Hydrogenation and Catalysis
- Chemical Synthesis and Reactions
- Coordination Chemistry and Organometallics
- Chemical Synthesis and Analysis
- Catalytic Alkyne Reactions
- Crystallography and molecular interactions
- Organic Chemistry Cycloaddition Reactions
- Conducting polymers and applications
- Synthesis and Catalytic Reactions
- Electrochemical Analysis and Applications
- Electrocatalysts for Energy Conversion
- Innovative Microfluidic and Catalytic Techniques Innovation
- Organic Electronics and Photovoltaics
- Synthesis of heterocyclic compounds
- Nanomaterials for catalytic reactions
Okayama University
2016-2025
Division of Chemistry
2019
Okayama University of Science
2012-2016
Johannes Gutenberg University Mainz
2015
Davenport University
2006
University of Toronto
2006
Kyoto University
1999-2004
Kyoto Bunkyo University
1999
Kyoto University Institute for Chemical Research
1999
Abstract Catalysts that can promote acyl transfer processes are important to enantioselective synthesis and their development has received significant attention in recent years. Despite noteworthy advances, discovery of small-molecule catalysts robust, efficient, recyclable reactions with high enantioselectivity be easily cost-effectively prepared quantities (that is, >10 g) remained elusive. Here, we demonstrate by attaching a binaphthyl moiety, appropriately modified establish H-bonding...
A novel strategy for the diversity-oriented synthesis of multisubstituted olefins, where 2-pyridyldimethyl(vinyl)silane functions as a versatile platform olefin synthesis, is described. The palladium-catalyzed Heck-type coupling 2-pyridyldimethyl(vinyl)silanes with organic iodides took place in presence Pd2(dba)3/tri-2-furylphosphine catalyst to give beta-substituted vinylsilanes excellent yields. occurred even alpha- and 2-pyridyldimethyl(vinyl)silanes. one-pot double Heck two different...
Abstract The first electrochemical dehydrogenative C−S bond formation leading to thienoacene derivatives is described. Several were synthesized by C−H/S−H coupling. addition of n Bu 4 NBr, which catalytically promoted the reaction as a halogen mediator, was essential.
The first synthesis of nitrogen-bridged terthiophenes (NBTTs) has been achieved by a tandem Buchwald-Hartwig coupling 3,3',3",4'-tetrabromo-2,2':5',2"-terthiophene. Several NBTT derivatives bearing aryl or alkyl moieties on the N-atoms could be synthesized. Their fundamental electrochemical characteristics and HOMO-LUMO levels were found to influenced substituents N-atoms.
The first electrochemical synthesis of diarylphosphole oxides (DPOs) was achieved under mild conditions. practical protocol employs commercially available and inexpensive DABCO as a hydrogen atom transfer (HAT) mediator, leading to various DPOs in moderate good yields. This procedure can also be applied the six-membered phosphacycles, such phenophosphazine derivatives. Mechanistic studies suggested that reaction proceeds via an electro-generated phosphinyl radical.
ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTHighly Efficient Carbopalladation Across Vinylsilane: Dual Role of the 2-PyMe2Si Group as a Directing and Phase TagKenichiro Itami, Koichi Mitsudo, Toshiyuki Kamei, Tooru Koike, Toshiki Nokami, Jun-ichi YoshidaView Author Information Department Synthetic Chemistry Biological Kyoto University, Yoshida, 606-8501, Japan Cite this: J. Am. Chem. Soc. 2000, 122, 48, 12013–12014Publication Date (Web):November 17, 2000Publication History Received18...
Metal-catalyzed hydrosilylation of alkenes and alkynes using dimethyl(pyridyl)silane is described. The dimethyl(2-pyridyl)silane (2-PyMe2SiH) proceeded well in the presence a catalytic amount RhCl(PPh3)3 with virtually complete regioselectivity. By taking advantage phase tag property 2-PyMe2Si group, products were isolated greater than 95% purity by simple acid−base extraction. Strategic catalyst recovery was also demonstrated. 2-PyMe2SiH Pt(CH2CHSiMe2)2O/P(t-Bu)3 to give...
A variety of di- and trisubstituted thiophenes were synthesized by a one-pot palladium-catalyzed ortho-alkylation sequence terminated either Heck or C−H coupling. Initial results toward the functionalization indoles are also presented.
We have developed an electrooxidative method for generating cationic palladium complexes [Pd(CH3CN)4][X]2 (X = BF4, PF6, and ClO4) from Pd(OAc)2 several electrolytes bearing X groups in CH3CN. The system could be integrated into electrochemical Wacker-type reaction. In the presence of a catalytic amount TEMPO, reaction proceeded smoothly to give corresponding methyl ketones.
Chiral N,N-4-(dimethylamino)pyridine (DMAP) derivatives, which can be readily prepared by the Ugi multicomponent reaction in a one-pot manner, have been efficiently applied to enantioselective Steglich rearrangement of oxindole derivatives give desired products bearing quaternary carbon center high yield (>98% yield) and with enantioselectivity (up 99:1 er).
Cyanosilylation of carbonyl compounds provides protected cyanohydrins, which can be converted into many kinds such as amino alcohols, amides, esters, and carboxylic acids. In particular, the use trimethylsilyl cyanide sole carbon source avoid need for more toxic inorganic cyanides. this paper, we describe an electrochemically initiated cyanosilylation its application to a microflow reactor. Furthermore, identify suitable reaction conditions, reflect considerations beyond simply high yield,...
Electrochemical synthesis of dibenzothiophene derivatives was achieved. Several bis(biaryl) disulfides are efficiently converted to dibenzothiophenes by electrochemical oxidation. The use Bu4NBr as a halogen mediator essential, and wide varieties were obtained in good yields.
The production of cyclic amines, which are vital to the pharmaceutical industry, relies on energy-intensive thermochemical hydrogenation. Herein, we demonstrate electrocatalytic hydrogenation nitrogen-containing aromatic compounds, specifically pyridine, at ambient temperature and pressure via a membrane electrode assembly with an anion-exchange membrane. We synthesized piperidine using carbon-supported rhodium catalyst, achieving current density 25 mA cm–2 efficiency 99% under circular flow...
Now even unstrained alkenes can be used in catalytic intermolecular Pauson–Khand reactions [Eq. (a)]. This is made possible by the use of directing group dimethyl(2-pyridyl)silyl, which easily removed at end reaction. Furthermore, one observes completely regioselective incorporation substituents 4- and 5-positions 2-cyclopentenone structure. Supporting information for this article available on WWW under http://www.wiley-vch.de/contents/jc_2002/2002/z19338_s.pdf or from author. Please note:...
An electro-oxidative method for generating silver acetylides from acetylenes with a Ag anode was developed. The reaction could be integrated into Pd-catalysed electrochemical Sonogashira-type reaction. In the presence of catalytic amount Pd(OAc)2 and 4-BzO-TEMPO, electro-generated reacted immediately arylboronic acids to afford corresponding coupling adducts in high yields.
An efficient and simple protocol for the kinetic resolution of secondary alcohols is presented. The new system based on a combination chiral Brønsted acid, DABCO, acetyl chloride gives various enantioenriched with selectivity factors up to 105.
Electrochemical dehydrogenative C-O bond formation for the synthesis of sultones was achieved. In presence K2CO3 and H2O, constant current electrolysis [1,1'-biphenyl]-2-sulfonyl chloride afforded an aryl-fused sultone quantitatively. Under optimized conditions, a variety derivatives were obtained. Control experiments suggest that electrochemical oxidation sulfonates generated in situ would afford sulfo radical intermediates.
Abstract Electrochemical organic synthesis has attracted attention as an environmentally friendly method for constructing heterocyclic compounds via carbon–heteroatom bond formation. Herein, we describe the representative examples of electrochemical reactions to produce heterocycles and discuss them according whether they involve direct or indirect electrolysis.
Some circumstantial evidence for the directing effect of 2-pyridylsilyl group in Ru-catalyzed intermolecular Pauson-Khand-type reaction (PKR) alkenyl(2-pyridyl)silane, alkyne, and carbon monoxide has been provided. Most importantly, we have succeeded isolating several monometallic Ru complexes relevant to catalytic reaction: Ru(vinylsilane)(CO)(3) ruthenacyclopentene. While stoichimetric complex with an alkyne led formation corresponding cyclopentenone (PKR product) at 100 degrees C,...