18657-09-5

Upstream product

• 74-83-9 methyl bromide 
• 106175-54-6 1-(p-methoxyphenyl)propenyl-lithium 
• 3179-10-0 (E)-1-methoxy-4-(2-nitrovinyl)benzene 
• 557-20-0 diethylzinc 
• 17271-36-2 2-[(propyl)sulfonyl]-1,3-benzothiazole 
• 123-11-5 4-methoxy-benzaldehyde 
• 6228-47-3 n-propyltriphenylphosphonium bromide 
• 5271-36-3 P,P-diethyldibenzophospholium iodide 
• 123-38-6 propionaldehyde 
• 156050-38-3 2-<(4-methoxyphenyl)methylsulfonyl>benzothiazole 
• 80-48-8 methyl p-toluene sulfonate 
• 3815-30-3 4-(4-methoxyphenyl)-3-buten-2-one 
• 3179-10-0 1-methoxy-4-(2-nitro-vinyl)-benzene 
• 1115-99-7 triethyl gallium 

Relevant academic research and scientific papers

Facile Synthesis of Chiral Arylamines, Alkylamines and Amides by Enantioselective NiH-Catalyzed Hydroamination

Regio- and enantioselective hydroarylamination, hydroalkylamination and hydroamidation of styrenes have been developed by NiH catalysis with a simple bioxazoline ligand under mild conditions. A wide range of enantioenriched benzylic arylamines, alkylamines and amides can be easily accessed by nitroarenes, hydroxylamines and dioxazolones, respectively as amination reagents. The chiral induction in these reactions is proposed to proceed through an enantiodifferentiating syn-hydronickellation step.

Selecting double bond positions with a single cation-responsive iridium olefin isomerization catalyst

The catalytic transposition of double bonds holds promise as an ideal route to alkenes of value as fragrances, commodity chemicals, and pharmaceuticals; yet, selective access to specific isomers is a challenge, normally requiring independent development of different catalysts for different products. In this work, a single cation-responsive iridium catalyst selectively produces either of two different internal alkene isomers. In the absence of salts, a single positional isomerization of 1-butene derivatives furnishes 2-alkenes with exceptional regioselectivity and stereoselectivity. The same catalyst, in the presence of Na+, mediates two positional isomerizations to produce 3-alkenes. The synthesis of new iridium pincer-crown ether catalysts based on an aza-18-crown-6 ether proved instrumental in achieving cation-controlled selectivity. Experimental and computational studies guided the development of a mechanistic model that explains the observed selectivity for various functionalized 1-butenes, providing insight into strategies for catalyst development based on noncovalent modifications.

Cobalt-Catalyzed Z to e Isomerization of Alkenes: An Approach to (E)-β-Substituted Styrenes

An efficient cobalt-catalyzed Z to E isomerization of β-substituted styrenes using the amido-diphosphine ligand was developed, delivering the (E)-isomers with good functional tolerance and high stereoselectivity. The reaction could be scaled up to gram-scale with a catalyst loading of 0.1 mol %, using a mixture of (Z)- and (E)-alkene as the starting material. Preliminary mechanistic studies indicated that cobalt(I)-hydride and a benzylic-cobalt species were probably involved in the reaction, as supported by experiments and DFT calculations.

RETRACTED ARTICLE: Copper-Catalyzed Decarboxylative C(sp2)-C(sp3) and C(sp)-C(sp3) Coupling of Substituted Cinnamic Acids and 3-Phenyl Propiolic Acid with N-Tosyl Oxaziridines

A mild and efficient strategy for decarboxylative C(sp2)-C(sp3) and C(sp)-C(sp3) coupling of α,β-unsaturated carboxylic acids such as substituted cinnamic acids and 3-phenyl propiolic acid with N-Tosyl oxaziridines was developed. The corresponding products were achieved in moderate to good yields with excellent stereoselectivity. Base-free and oxidant-free conditions allow good functional group tolerance. Radical inhibitors such as TEMPO and BHT completely suppressed the reactions suggesting a radical mechanism was involved. This study is supposed to broaden the frontier of oxaziridines' chemistry and to open up a novel cascade for alkylating reagents.

Controllable Isomerization of Alkenes by Dual Visible-Light-Cobalt Catalysis

We report herein that thermodynamic and kinetic isomerization of alkenes can be accomplished by the combination of visible light with Co catalysis. Utilizing Xantphos as the ligand, the most stable isomers are obtained, while isomerizing terminal alkenes over one position can be selectively controlled by using DPEphos as the ligand. The presence of the donor–acceptor dye 4CzIPN accelerates the reaction further. Transformation of exocyclic alkenes into the corresponding endocyclic products could be efficiently realized by using 4CzIPN and Co(acac)2 in the absence of any additional ligands. Spectroscopic and spectroelectrochemical investigations indicate CoI being involved in the generation of a Co hydride, which subsequently adds to alkenes initiating the isomerization.

Orthogonally protected 1,2-diols from electron-rich alkenes using metal-free olefin syn-dihydroxylation

A new method for the stereoselective metal-free syn-dihydroxylation of electron-rich olefins is reported, involving reaction with TEMPO/IBX in trifluoroethanol (TFE) or hexafluoroisopropanol (HFIP) and the addition of a suitable nucleophile. Orthogonally

Direct fluorination of styrenes

We have developed a practical method to synthesize fluorostyrene compounds. A mild and regioselective mono-fluorination reaction occurred smoothly for various di- and trisubstituted styrenes in the presence of RuCl3 and N-fluorobenzenesulfonimide (NFSI). A tandem alkyne hydroarylation-olefin fluorination reaction was also developed using an Au catalyst.

Photocatalytic synthesis of dihydrobenzofurans by oxidative [3+2] cycloaddition of phenols

We report a protocol for oxidative [3+2] cycloadditions of phenols and alkenes applicable to the modular synthesis of a large family of dihydrobenzofuran natural products. Visible-light-activated transition metal photocatalysis enables the use of ammonium persulfate as an easily handled benign terminal oxidant. The broad range of organic substrates that are readily oxidized by photoredox catalysis suggests that this strategy may be applicable to a variety of useful oxidative transformations.

Alkyl transfer from C-C cleavage: Replacing the nitro group of nitro-olefins

Alkyl substituted Hantzsch esters are rationally used as alkylation reagents to replace the nitro groups of nitro olefins to give excellent yields of trans-olefins. The reaction mechanism is considered to proceed through a free radical mechanism, which is different from the corresponding transfer alkylation of imines. This journal is the Partner Organisations 2014.

Pd0-mediated rapid coupling of methyl iodide with excess amounts of benzyl- and cinnamylboronic acid esters: Efficient method for incorporation of positron-emitting 11C radionuclide into organic frameworks by coupling between two sp<

Pd0-mediated rapid cross coupling between sp3- hybridized carbons of CH3I and benzyl- or cinnamylboronic acid esters using [Pd{P(tert-C4H9)3}2]/CsF in DMF/H2O gave the