A5051371490- Cyclopropane Reaction Mechanisms
- Catalytic C–H Functionalization Methods
- Synthesis and Catalytic Reactions
- Oxidative Organic Chemistry Reactions
- Phenothiazines and Benzothiazines Synthesis and Activities
- Chemical Synthesis and Reactions
- Innovative Microfluidic and Catalytic Techniques Innovation
- Electrochemical Analysis and Applications
- Asymmetric Hydrogenation and Catalysis
- Chemical Reaction Mechanisms
- Electrocatalysts for Energy Conversion
- Radical Photochemical Reactions
- Sulfur-Based Synthesis Techniques
- Mesoporous Materials and Catalysis
- Chemical Reactions and Mechanisms
- Fluorine in Organic Chemistry
- Multicomponent Synthesis of Heterocycles
Université Laval
2019-2024
Département de Chimie Moléculaire
2019
Fe(OTf)<sub>2</sub>was used to catalyze the insertion reaction of α-diazocarbonyls into S–H bonds at 40 °C.
The insertion reaction of a broad range diazo compounds into Si-H bonds was found to be efficiently catalysed by Fe(OTf)2 in an emerging green solvent i.e. dimethyl carbonate (DMC). α-silylated products were obtained good excellent yields (up 95%). Kinetic studies showed that the extrusion N2 form iron carbene intermediate is rate-limiting. iron-catalysed methyl α-phenyl-α-diazoacetate polar X-H (S-H, N-H, and O-H) also established DMC.
An electrochemical synthesis of diazo compounds from hydrazones in yields as high 99% was performed. This method elaborated a useful synthetic and demonstrated on various (24 examples). Apart exhibiting an efficiency that matched commonly used harsh toxic chemical oxidants, this reaction is practically simple to set up, requires mild conditions, highly electron efficient (3 F/mol).
An efficient synthesis of 3-trifluoromethyl-3-aryl-cyclopropenes via the cyclopropenation reaction alkynes with photolytically generated carbenes from diazirine compounds is described. This performed in continuous flow using readily available LEDs under mild conditions. new and method describes 25 examples yields up to 97%, achieved a 5 min residence time. Control experiments highlighted that diazirines are more than diazo for this transformation.
We report a new electrochemical supporting-electrolyte-free method for synthesizing ureas, carbamates, and thiocarbamates via the oxidation of oxamic acids. This simple, practical, phosgene-free route includes generation an isocyanate intermediate in situ anodic decarboxylation acid presence organic base, followed by one-pot addition suitable nucleophiles to afford corresponding thiocarbamates. procedure is applicable different amines, alcohols, thiols. Furthermore, when single-pass...
Abstract The use of iron catalysis to enable reactions with diazo compounds has emerged as a valuable tool forge carbon–carbon or carbon–heteroatom bonds. While are often encountered toxic and expensive metal catalysts, such Rh, Ru, Pd, Ir, Cu, resurgence Fe been observed. This short review will showcase highlight the recent advances in iron-mediated compounds. 1 Introduction 2 Insertion Reactions 2.1 into B–H Bonds 2.2 Si–H 2.3 N–H 2.4 S–H bonds 3 Ylide Formation Subsequent 3.1 Doyle–Kirmse...
A new bismuth(V) oxidative catalytic system has been developed and applied for the conversion of hydrazones into diazo compounds. With use low amounts Ph3Bi AcOH with NaBO3·H2O as a terminal oxidant, in situ formation Ph3Bi(OAc)2 is capable oxidizing excellent yields. The reaction was synthesis diazocarbonyls 2,2,2-trifluoromethyl diazoalkanes good to
A new electrochemical method for the preparation of isocyanides from easily accessible aminotetrazole derivatives has been developed, which tolerates an unprecedented range functional groups. The use chemical, rather than electrochemical, oxidation to afford was also demonstrated, provides access these compounds those without electrosynthesis equipment. practicality scale-up using flow electrochemistry in addition possibility electrochemically generated further reactions.
Aryl-ester acylhydrazones readily react with phenyl iododiacetate (PIDA) in methanol to produce the corresponding α-diazoesters good excellent yields (30 examples). The conditions have also been proven be efficient synthesis of triazolopyridines. crude mixture containing diazo compound and acetic acid was irradiated low-energy blue LED light for a subsequent one-pot insertion situ-generated carbene AcOH afford respective acetates high yields.
An original metal-free regio- and stereoselective intermolecular hydroamination of alkynes is described. Various (E)-enamines were obtained from arylacetylenes aliphatic secondary amines in the presence ethylene glycol as a solvent. The latter assumed to play major role mechanism through hydrogen bonding proton exchange.