105561-41-9

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 530-48-3 1,1-Diphenylethylene 
• 119-61-9 benzophenone 
• 908093-98-1 diazodiphenylmethane 
• 140-88-5 ethyl acrylate 
• 17792-17-5 ethyl 3,3-diphenylacrylate 
• 5350-57-2 benzophenone hydrazone 

Downstream Products

• 7150-12-1 2,2-diphenyl-cyclopropanecarboxylic acid 
• 37555-48-9 2,2-diphenylcyclopropylmethanol 
• 936140-30-6 (E)-3-(2,2-diphenylcyclopropyl)prop-2-en-1-ol 
• 934009-26-4 [2-(2,2-dibromovinyl)-1-phenylcyclopropyl]benzene 
• 119981-84-9 ethyl (E)-3-(2,2-diphenylcyclopropyl)acrylate 
• 936140-31-7 (E)-N-tert-butyl-3-(2,2-diphenylcyclopropyl)prop-2-en-1-amine 
• 936140-32-8 methyl 3-(tert-butyl((E)-3-(2,2-diphenylcyclopropyl)-2-propenyl)amino)-3-oxopropanoate 
• 934009-31-1 1-{2-[2-(triisopropylsilyl)ethynyl]phenyl}-3-(2,2-diphenylcyclopropyl)prop-2-yn-1-ol 
• 934009-16-2 1-{2-[2-(triisopropylsilyl)ethynyl]phenyl}-3-(2,2-diphenylcyclopropyl)prop-2-ynyl acetate 
• 934009-17-3 bis(4-bromophenyl)(4-{1-(2,2-diphenylcyclopropyl)-3-[(2-triisopropylsilanylethynyl)phenyl]-propa-1,2-dienyl}phenyl)amine 
• 59591-01-4 2,2-diphenylcyclopropanecarbaldehyde 
• 93319-68-7 1,1'-(2-ethynylcyclopropane-1,1-diyl)dibenzene 
• 53017-55-3 N-β-Hydroxyethyl-2,2-diphenyl cyclopropane carboxamide 
• 1047663-25-1 (2,2-diphenylcyclopropyl)-bis(4-methyl-2-thiazolyl)carbinol 

Relevant academic research and scientific papers

From homogeneously to heterogeneously catalyzed cyclopropanation reactions: New polymeric membranes embedding cobalt chiral schiff base complexes

In this paper we report the preparation of catalytic polymeric membranes having the complex [(N,N′-bis(3-tert-butyl-5-(heptadecafluorooctyl)salicylidene)-trans-1,2-cyclohexanediamine)Co] embedded into Hyflon AD60X, PES and PSf and their use in the cyclopr

First synthesis of a carbohydrate-derived pyridyl bis(thiazoline) ligand

The first synthesis of a carbohydrate-based pyridyl bis(thiazoline) ligand starting from d-glucosamine and its application in asymmetric cyclopropanation reactions are reported.

Unexpected formation of a μ-carbido diruthenium(IV) complex during the metalation of phthalocyanine with Ru3(CO)12 and its catalytic actIVity in carbene transfer reactions

A μ-carbido diruthenium(iv) phthalocyanine complex was prepared for the first time from the free-base octabutoxyphthalocyanine by direct metalation with Ru3(CO)12. The first examples of the catalytic activity of Ru(iv) binuclear phthalocyanines were demonstrated by the cyclopropanation of aromatic olefins and carbene insertion into the N-H bonds of aromatic or aliphatic amines with turnover numbers of 680-1000 and 580-1000, respectively.

Cyclopropanation of olefins with diazoalkanes, catalyzed by CoII(porphyrin) complexes - A synthetic and mechanistic investigation and the molecular structure of CoIII(TPP)(CH2CO2Et) (TPP = dianion of meso-tetrap

Cobalt(II) porphyrin complexes catalyze reactions between ethyl diazoacetate (EDA) and styrenes to give the corresponding cyclopropanes with trans selectivity. The reactions of other diazoalkanes and other olefins have also been carried out, and the mecha

The tandem intermolecular Paterno-Buechi reaction: Formation of tetrahydrooxepins

The Paterno-Buechi reaction is the [2 + 2] photocycloaddition between carbonyl compounds and electron rich alkenes to generate oxetane products. By the introduction of substituted cyclopropyl rings to the alkene components, the utility of this reaction has been extended to facilitate the synthesis of substituted tetrahydrooxepins. It is proposed that initial addition of oxygen radicals to cyclopropyl enol ethers generates cyclopropylmethyl radicals which, when the cyclopropane ring bears appropriate radical-stabilising groups (e.g. phenyl, CO2Et), undergo rapid fragmentation to form homoallylic 1,7-biradicals which then recombine to deliver the observed tetrahydrooxepin products. The importance of various radical-stabilising substituents on the efficiency of tetrahydrooxepin formation is examined.

Asymmetric cyclopropanation of styrenes catalyzed by metal complexes of D2-symmetrical chiral porphyrin: Superiority of cobalt over iron

(Chemical Equation Presented) The cobalt(II) complex of D 2-symmetric chiral porphyrin [Co(1)] is an effective catalyst for highly diastereoselective and enantioselective cyclopropanation of a broad range of styrene derivatives under mild conditions. Dimerization of diazo compounds, a common side reaction in metal-mediated carbene transfer processes, is minimized in a cobalt porphyrin-based system, obviating the need to employ excess substrates and slow addition of diazo compounds. The high catalytic activity and selectivity of [Co(1)] evidently resulted from the appropriate combination of the cobalt ion and the chiral porphyrin 1 as the use of iron(III) complex of the same ligand [Fe(l)Cl] afforded the desired cyclopropane products in low yields and poor enantioselectivity.

Transition Metal-Catalyzed Cyclopropanation of Alkenes in Water: Catalyst Efficiency and in Situ Generation of the Diazo Reagent

(Matrix Presented) A cyclopropanation reaction involving ethyl diazoacetate and olefins proceeds with surprisingly high efficiency in aqueous media using| Rn(II) carboxylates. Nishiyama's Ru(II) Py box and Katsuki's Co(II) Salen complexes that allow for highly enantioselective cyclopropanations in organic solvents can also be applied to aqueous cyclopropanations with similar results. In situ generate of ethyl diazoacetate and cyclopropanation also proceeds efficiently. A chemoselective O-H insertion is also possible in water when hydrophobic catalysts and alcohols are used.

Catalytic and asymmetric cyclopropanation of styrenes catalysed by ruthenium porphyrin and porphycene complexes

Ruthenium porphyrin and porphycene complexes catalyse stereospecific cyclopropanation of styrenes; high product turnovers with up to 90.8% ee were achieved with the [Ru(P*)(CO)(EtOH)] catalyst (H2P* = chiral D4 porphyrin).

Synthesis of new copper(i) complexes with tris(2-pyridyl) ligands. Applications to carbene and nitrene transfer reactions

New copper(i) complexes with tris(2-pyridyl)methane (TPC), tris(2-pyridyl)methoxymethane (TPM) and tris(2-pyridyl)amine (TPN) ligands have been synthesized and characterized, including structural determinations by X-ray diffraction of some examples. Their activity as catalysts in carbene and nitrene transfer reactions was studied.

Selective carbene transfer to amines and olefins catalyzed by ruthenium phthalocyanine complexes with donor substituents

Electron-rich ruthenium phthalocyanine complexes were evaluated in carbene transfer reactions from ethyl diazoacetate (EDA) to aromatic and aliphatic olefins as well as to a wide range of aromatic, heterocyclic and aliphatic amines for the first time. It was revealed that the ruthenium octabutoxyphthalocyanine carbonyl complex [(BuO)8Pc]Ru(CO) is the most efficient catalyst converting electron-rich and electron-poor aromatic olefins to cyclopropane derivatives with high yields (typically 80-100%) and high TON (up to 1000) under low catalyst loading and nearly equimolar substrate/EDA ratio. This catalyst shows a rare efficiency in the carbene insertion into amine N-H bonds. Using a 0.05 mol% catalyst loading, a high amine concentration (1 M) and 1.1 eq. of EDA, a number of structurally divergent amines were selectively converted to mono-substituted glycine derivatives with up to quantitative yields and turnover numbers reaching 2000. High selectivity, large substrate scope, low catalyst loading and practical reaction conditions place [(BuO)8Pc]Ru(CO) among the most efficient catalysts for the carbene insertion into amines.