34221-26-6

Upstream product

• 53400-00-3 1-methoxy-4-((1RS,2SR)-2-phenylcyclopropyl)benzene 
• 670-54-2 ethenetetracarbonitrile 
• 100-42-5 styrene 
• 123-11-5 4-methoxy-benzaldehyde 
• 637-69-4 4-Methoxystyrene 
• 908094-04-2 phenyldiazomethane 
• 23304-25-8 p-methoxyphenyldiazomethane 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 19350-72-2 N'-(4-methoxybenzylidene)-4-methylbenzenesulfonohydrazide 
• 76973-46-1 5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazole 
• 1694-19-5 E-1-(phenyl)-2-(4'-methoxyphenyl)ethene 
• 25628-09-5 tetramethylammonium trifluoromethanesulphonate 
• 959-33-1 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one 
• 959-23-9 4'-methoxychalcone 

Downstream Products

• 86396-69-2 3-(4-methoxyphenyl)-5-phenyl-1,2-dioxolane 
• 86396-69-2 cis-3-(4-methoxyphenyl)-5-phenyl-1,2-dioxolane 
• 114424-49-6 cis-3,5-diphenyl-1,2-dioxolane 
• 20821-97-0 5-(4-methoxyphenyl)-3-phenyl-4,5-dihydroisoxazole 
• 101286-60-6 1-amino-3-(p-methoxyphenyl)-1-phenylpropane 

Relevant academic research and scientific papers

Reductive Ring-Opening 1,3-Difunctionalizations of Arylcyclopropanes with Sodium Metal

Sodium dispersion promotes reductive ring opening of arylcyclopropanes. The presence of a reduction-resistant electrophile, such as methoxypinacolatoborane, epoxide, oxetane, paraformaldehyde, or chlorotrimethylsilane, during the reductive ring opening event leads to the formation of 1,3-difunctionalized 1-arylalkanes by immediate trappings of the resulting two reactive carbanions. In particular, the ring-opening 1,3-diborylations of arylcyclopropanes afford 1,3-diborylalkanes with high syn selectivity.

Modular enantioselective synthesis of cis-cyclopropanes through self-sensitized stereoselective photodecarboxylation with benzothiazolines

Chiral cis-cyclopropanes are strained rigid analogues of alkyl chains, whose study and application are limited by their difficult synthesis. A modular approach from olefin materials is enabled by the discovery of the electron donor-acceptor (EDA) interaction between 2-substituted benzothiazolines and N-hydroxyphthalimide esters. These complexes are activated by visible light without photocatalysts, and the benzothiazoline reagent plays a triple role as a photoreductant, a stereoselective hydrogen-atom donor, and a Br?nsted acid. Beyond the enantioselective synthesis of cis-cyclopropanes, these results introduce benzothiazolines as accessible and easily tunable self-sensitized photoreductants.

Iron-catalyzed synthesis of cyclopropanes by in situ generation and decomposition of electronically diversified diazo compounds

The modular synthesis of a variety of trans 1,2-disubstituted cyclopropanes in a safe and user-friendly one-pot iron-catalyzed cyclopropanation reaction is described. Easily synthesized N-nosylhydrazones are used as diazo precursors, allowing the in situ generation of electron-rich diazo compounds under mild reaction conditions and their direct participation in the cyclopropanation reaction.

Improved zinc-catalyzed simmons-smith reaction: Access to various 1,2,3-trisubstituted cyclopropanes

The Simmons-Smith reaction of zinc carbenoids with alkenes is a powerful method to access cyclopropanes containing various substitution patterns. This work exploits the high reactivity of aryldiazomethanes toward zinc halides to generate aryl-substituted carbenoids catalytically. These carbenoids are able to cyclopropanate various alkenes diastereoselectively, including unfunctionalized substrates such as styrenes. The zinc catalyst can be modified to tolerate the use of free allylic alcohols.

Cyclopropanation of styrenes and stilbenes using lithiomethyl trimethylammonium triflate as methylene donor

Lithiomethyl trimethylammonium triflate, prepared from tetramethylammonium triflate, cyclopropanates several styrenes and stilbenes with electron-donating and selected electron-withdrawing substituents efficiently. Kinetic data support a stepwise nucleophilic addition-ring closure mechanism for this methylenation. This journal is the Partner Organisations 2014.

Intermolecular metal-free cyclopropanation of alkenes using tosylhydrazones

We describe the first general method for the metal-free cyclopropanation of alkenes by using N-tosylhydrazones as an in situ source of diazo compounds. This new method works with a wide variety of alkenes (styrene derivatives, dienes, enynes, and electron-deficient alkenes) by using N-tosylhydrazones derived from various ketones or aldehydes (aromatic, aliphatic, enones). The reaction is performed with the use of K2CO3 as a base to form the diazo species and is compatible with a wide array of functional groups. A new procedure for the synthesis of cyclopropanes by the formal cyclopropanation of carbonyl compounds and alkenes is described. This metal-free reaction proceeds through the base-promoted decomposition of tosylhydrazones. There is significant tolerance of the functional groups, enabling cyclopropanation in the presence of functionalities often not compatible with other methodologies.

Olefin cyclopropanation with aryl diazocompounds upon catalysis by a dirhodium(II) complex

A dirhodium(II) complex with N-perfluorooctylsulfonylprolinate ligands is found to catalyze the cyclopropanation of olefins with simple aryl diazomethanes. In contrast to previously reported dirhodium(II) catalysts, the present complex works well not only with very electron-rich olefins such as enol ethers, but also with styrenes. Consequently, the present catalyst allows to prepare functionalized diarylcyclopropanes in moderate yields with good diastereoselectivity for the cis product, whereas the enantioselectivity of the reaction appears negligible.

Gold-catalyzed annulation/fragmentation: Formation of free gold carbenes by retro-cyclopropanation

The gold(I)-catalyzed cyclization of 1-(prop-2-yn-1-yl)-2-alkenylbenzenes substituted at the benzylic position with OR groups gives 1,3-disubstituted naphthalenes with concomitant fragmentation of the alkene. One of these annulations proceeds by a retro-cyclopropanation that leads to free gold(I) carbenes.

Simultaneous Capture of Two Distinct Radical Ion Intermediates Generated from the EDA Complexes of Three-Membered Compounds with TCNE by Photoexcitation and in the Dark

Irradiation of the electron donor-acceptor (EDA) complexes of 2,2-diaryl-1-methylenecyclopropanes, 1,1,2,2-tetraarylcyclopropanes, 2,3-diaryloxiranes, or 2,3-diarylaziridines with tetracyanoethylene (TCNE) under aerated conditions involved oxygenation and