120522-83-0

Upstream product

• 100-42-5 styrene 
• 22979-35-7 Methyl phenyldiazoacetate 
• 688361-77-5 (1S)-1,2-diphenyl-cycloprop-2-enecarboxylic acid methyl ester 
• 42333-02-8 trans-1,2-diphenyl-1-cyclopropanecarboxylic acid 
• 77-78-1 dimethyl sulfate 
• 616-45-5 2-pyrrolidinon 
• 91-56-5 indole-2,3-dione 
• 18793-81-2 methyl 2-phenyl-2-(2-tosylhydrazono)acetate 
• 108-95-2 phenol 
• 36854-27-0 2,3-diphenylacrylic acid methyl ester 
• 1774-47-6 trimethylsulfoxonium iodide 
• 91-47-4 2,3-diphenylacrylic acid 
• 101-41-7 benzeneacetic acid methyl ester 
• 536-74-3 phenylacetylene 

Downstream Products

• 42333-01-7 (E)-1,2-diphenylcyclopropanecarboxylic acid 
• 42333-02-8 trans-1,2-diphenyl-1-cyclopropanecarboxylic acid 
• 40164-60-1 methyl 2,4-diphenylbutanoate 
• 55753-44-1 (2,4-Diphenyl-butyl)-dimethyl-amine 
• 87395-79-7 (+)-(E)-1-acetyl-1,2-diphenylcyclopropane 
• 87395-78-6 (+)-(Z)-1-acetyl-1,2-diphenylcyclopropane 
• 87421-62-3 (+)-(Z)-1-cyano-1,2-diphenylcyclopropane 
• 87421-65-6 (-)-(E)-1-cyano-1,2-diphenylcyclopropane 
• 10223-76-4 (1S,2S)-1,2-Diphenyl-cyclopropanecarboxylic acid amide 
• 10223-76-4 (1S,2R)-1,2-Diphenyl-cyclopropanecarboxylic acid amide 
• 10224-13-2 1,2-Diphenyl-cyclopropan-1-carbonsaeure 
• 1413940-37-0 C₂₁H₂₄N₂O 

Relevant academic research and scientific papers

Bis(imino)pyridine iron complexes for catalytic carbene transfer reactions

The bis(imino)pyridine iron complex, for the first time, is developed as an effective metal carbene catalyst for carbene transfer reactions of donor-acceptor diazo compounds. Its broad catalytic capability is demonstrated by a range of metal carbene reactions, from cyclopropanation, cyclopropenation, epoxidation, and Doyle-Kirmse reaction to O-H insertion, N-H insertion, and C-H insertion reactions. The asymmetric cyclopropanation of styrene and methyl phenyldiazoacetate was successfully achieved by the new chiral bis(imino)pyridine iron catalyst, which delivers a new gateway for the development of chiral iron catalysis for metal carbene reactions.

Effect of rhodium carbenoid structure on cyclopropanation chemoselectivity

Rhodium-stabilized carbenoids derived from aryldiazoacetates and vinyldiazoacetates undergo highly chemoselective intermolecular cyclopropanations, and this selectivity has been quantified by a Hammett study. These donor/acceptor substituted carbenoids are much more chemoselective than the traditional carbenoids derived from alkyl diazoacetates. (C) 2000 Published by Elsevier science Ltd.

Cu-iminopyridine complexes as catalysts for carbene and nitrene transfer reactions

Copper complexes with chiral iminopyridine ligands were screened for their catalytic efficiency in carbene (cyclopropanation) and nitrene transfer reactions (aziridination, CH amidation). Both pre-formed and in situ formed complexes were considered. The r

Universal strategy for the immobilization of chiral dirhodium catalysts

(Chemical Equation Presented) Chiral rhodium(II) catalysts used in asymmetric carbenoid chemistry can be efficiently heterogenized using a novel immobilization strategy. The immobilized catalysts display similar reactivity and stereoselectivity to their h

Catalytic Asymmetric Cyclopropanation Using Bridged Dirhodium Tetraprolinates on Solid Support

(Matrix Presented) Dirhodium tetraprolinates in highly cross-linked macroporous polystyrene resins are very effective catalysts for asymmetric cyclopropanation using methyl aryldiazoaceates.

Dirhodium paddlewheel with functionalized carboxylate bridges: New building block for self-assembly and immobilization on solid support

A new dirhodium(II,II) paddlewheel complex, [Rh2(O 2CC6H4COOC2H5) 4] (1), has been synthesized using a predesigned functionalized carboxylate, namely, 4-(ethoxycarbonyl)benzoate. The target product has been crystallized from the acetone solution and structurally characterized as a bis-acetone adduct, [Rh2(O2CC6H 4COOC2H5)4(OCMe2) 2]C6H14 (2). By utilizing the ability of dangling ester groups to coordinate to open axial ends of neighboring dirhodium units, 1 can self-assemble to form 2D networks upon crystallization from solutions of noncoordinating solvents such as chlorobenzene and chloroform. The resulting [Rh2(O2CC6H4COOC 2H5)4]2C6H5Cl (3) and [Rh2(O2CC6H4COOC 2H5)4]2CHCl3 (4) products have microporous solid state structures with the pores filled with the corresponding disordered solvent molecules. Notably, 3 and 4 represent unique examples of 2D extended frameworks based on dirhodium tetracarboxylate paddlewheel units devoid of any exogenous ligands. In solution, the dangling ends of carboxylate bridges of 1 have been successfully utilized for condensation reaction with the selected solid support, benzylamine-functionalized polystyrene, allowing successful heterogenization of dirhodium units through the equatorial covalent attachment to the substrate. The resulting solid product was tested as a catalyst in the cyclopropanation reaction of styrene with methyl phenyldiazoacetate to show good yields and diastereoselectivity.

Effect of catalyst on the diastereoselectivity of methyl phenyldiazoacetate cyclopropanations

In contrast to previously published studies, the diastereoselectivity of phenyldiazoacetate cyclopropanations is not greatly altered by the type of rhodium carboxylate catalyst that is used.

Rh(II) catalysts with 4-hydroxyproline-derived ligands

Three new chiral Rh(II) catalysts with 4-hydroxyproline-derived ligands have been synthesised through a short and efficient synthetic route. The catalysts give good yields and ees in C-H insertion and cyclopropanation reactions, and their properties indicate an all-up reactive conformation of proline- and 4-hydroxyproline-derived Rh(II) catalysts.

Polynuclear copper(I) complexes with chelating bis- and tris-N-heterocyclic carbene ligands: Catalytic activity in nitrene and carbene transfer reactions

Di- and trinuclear complexes of copper(I) bearing bis- or tris-N-heterocyclic carbene ligands have been prepared and evaluated as catalysts in nitrene transfer reactions from PhI=NTs to unsaturated and saturated substrates (olefin aziridination and C-H bond amidation) and carbene transfer reactions from diazo compounds to olefins. The complexes exhibited moderate-to-high catalytic activity in both processes. The tosylamidation of C-H bonds, previously unreported with a NHC-containing copper catalyst, was promoted by the dinuclear complexes. Polynuclear oligo-NHC-copper complexes catalyse the transfer of carbene or nitrene fragments to unsaturated and saturated substrates. The first example of the tosylamidation of C-H bonds with a catalyst containing the NHCCu core is described. Copyright

Chiral catalysts for enantioselective intermolecular cyclopropanation reactions with methyl phenyldiazoacetate. Origin of the solvent effect in reactions catalyzed by homochiral dirhodium(II) prolinates

The highest levels of enantiocontrol in intermolecular cyclopropanation reactions of methyl phenyldiazoacetate have been achieved with homochiral dirhodium(II) prolinates in pentane, the solvent effect for which (0.8 ± 0.2 kcal/mol) is associated with lig