117780-29-7

Upstream product

• 2855-19-8 Decyl-oxiran 
• 591-51-5 phenyllithium 
• 100-42-5 styrene 
• 112-29-8 1-bromo dodecane 
• 112-44-7 undecylaldehyde 
• 7016-55-9 benzyl-triethylphosphonium bromide 
• 112-41-4 1-dodecene 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 66003-76-7 Diphenyliodonium triflate 
• 2050-77-3 Iododecane 
• 765-03-7 1-dodecyne 
• 98-80-6 phenylboronic acid 
• 7217-71-2 1-phenyl-2-propenyl acetate 
• 39691-62-8 nonylmagnesium bromide 

Downstream Products

• 123-01-3 1-dodecylbenzene 

Relevant academic research and scientific papers

Titanocene-Catalyzed Alkylation of Aryl-Substituted Alkenes with Alkyl Halides

A new method for substitution of a vinylic hydrogen with an alkyl group (a Mizoroki-Heck type transformation) was developed by a titanocene catalyst in the presence of nBuMgCl. This reaction could proceed regio- and stereoselectively under mild conditions to afford E-olefins using primary and secondary alkyl halides. The reactions of aliphatic alkenes, e.g., 1-octene and internal alkenes, were sluggish. When t-alkyl halides were employed, alkylative dimerization of alkenes proceeded exclusively to give symmetrical vic-diarylalkanes. These reactions involved addition of alkyl radicals to arylalkenes to form benzyl radicals as a carbon-carbon bond-forming step. Dimerization of thus formed benzyl radicals afforded symmetrical alkanes and β-hydrogen elimination from benzyltitanocene intermediates gave alkylated alkenes. A possibility that titanocene activates alkenes as radical accepters was also proposed.

Stereospecific Substituted Alkene Synthesis by Organo Lithium Reductive Alkylation of Epoxides

Stereospecifically alkylated olefins were synthesized in good yields by reaction of various epoxides with organolithium reagents with concommitant introduction of the alkyl group.

Electro-mediated PhotoRedox Catalysis for Selective C(sp3)–O Cleavages of Phosphinated Alcohols to Carbanions

We report a novel example of electro-mediated photoredox catalysis (e-PRC) in the reductive cleavage of C(sp3)?O bonds of phosphinated alcohols to alkyl carbanions. As well as deoxygenations, olefinations are reported which are E-selective and can be made Z-selective in a tandem reduction/photosensitization process where both steps are photoelectrochemically promoted. Spectroscopy, computation, and catalyst structural variations reveal that our new naphthalene monoimide-type catalyst allows for an intimate dispersive precomplexation of its radical anion form with the phosphinate substrate, facilitating a reactivity-determining C(sp3)?O cleavage. Surprisingly and in contrast to previously reported photoexcited radical anion chemistries, our conditions tolerate aryl chlorides/bromides and do not give rise to Birch-type reductions.

Iron-catalysed allylation-hydrogenation sequences as masked alkyl-alkyl cross-couplings

An iron-catalysed allylation of organomagnesium reagents (alkyl, aryl) with simple allyl acetates proceeds under mild conditions (Fe(OAc)2 or Fe(acac)2, Et2O, r.t.) to furnish various alkene and styrene derivatives. Mechanistic studies indicate the operation of a homotopic catalyst. The sequential combination of such iron-catalysed allylation with an iron-catalysed hydrogenation results in overall C(sp3)-C(sp3)-bond formation that constitutes an attractive alternative to challenging direct cross-coupling protocols with alkyl halides.

Preparation method of inactive alkene aryl compound

The invention discloses a preparation method of an inactive alkene aryl compound. The preparation method comprises steps as follows: arylboronic acid and inactive alkene are taken as raw materials andsubjected to an oxidization Heck reaction with a mechan

Ni-Catalyzed regio- and stereoselective addition of arylboronic acids to terminal alkynes with a directing group tether

Addition of arylboronic acids to directing group tethered acetylenes in a regio and stereoselective manner using an inexpensive catalytic system is achieved for the first time to access highly sought after allyl/homoallyl alcohol/amine units. The apparent vinylnickel intermediate was successfully trapped by the Michael electrophiles to get defined tri- and tetra-substituted olefins. An interesting selectivity switch was observed with internal alkynes.

Wittig Reactions of Trialkylphosphine-derived Ylides: New Directions and Applications in Organic Synthesis

The development of semi-stabilized, stabilized, and functionalized ylides derived from short-chain trialkylphosphines in the Wittig-type olefination reactions toward the synthesis of alkenes, including stilbenes, styrenes, and 1,3-dienes, as well as reagents for homologation reactions, are described. The methods allow easy access to alkenes with high (E)-stereoselectivity in good yield. These reactions are conducted with weak bases in aqueous media, which allows easy separation of water-soluble phosphine oxides. The development of a mild organocatalytic process for the Wittig reaction and extension toward the preparation of reporter stilbenes under biological conditions are also described. Applications toward the preparation of biologically active natural products and derivatives are discussed.

Z -selective olefin synthesis via iron-catalyzed reductive coupling of alkyl halides with terminal arylalkynes

Selective catalytic synthesis of Z-olefins has been challenging. Here we describe a method to produce 1,2-disubstituted olefins in high Z selectivity via reductive cross-coupling of alkyl halides with terminal arylalkynes. The method employs inexpensive and nontoxic catalyst (iron(II) bromide) and reductant (zinc). The substrate scope encompasses primary, secondary, and tertiary alkyl halides, and the reaction tolerates a large number of functional groups. The utility of the method is demonstrated in the synthesis of several pharmaceutically relevant molecules. Mechanistic study suggests that the reaction proceeds through an iron-catalyzed anti-selective carbozincation pathway.

Palladium-catalyzed intermolecular Heck reaction of alkyl halides

Intermolecular Heck reaction of common alkyl halides, a longstanding problem in palladium catalysis, is realized with a simple Pd/dppf catalyst. Both primary and secondary alkyl halides are suitable for coupling with aromatic olefins. Single electron transfer from (dppf)Pd0 to alkyl halide initiated the catalytic cycle and gave alkyl radicals. This journal is the Partner Organisations 2014.

Microwave-assisted palladium-catalyzed arylation of styrenes and alkenes with diaryliodonium salts

Highly effective microwave-assisted palladium-catalyzed arylation of styrenes and alkenes with diaryliodonium salts have been developed, giving styrenes in high yields without ligand in 60 s.