74725-45-4

Upstream product

• 33689-28-0 cyclobutane-1,2-dione 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 57951-63-0 1-(phenylethynyl)cyclopropan-1-ol 
• 536-74-3 phenylacetylene 
• 1191-95-3 cyclobutanone 
• 100-52-7 benzaldehyde 
• 611187-84-9 1-((E)-Styryl)-cyclopropanol 
• 7555-67-1 1-phenylmethylenecyclopropane 

Downstream Products

• 1402745-90-7 (E)-5,6-diphenyl-5-hexen-2-one 
• 98678-26-3 2-Benzylcyclobutan-1-one 
• 69063-22-5 (E)-5-benzylidene-γ-butyrolactone 

Relevant academic research and scientific papers

C-C bond activation by octacarbonyldicobalt: [3+1] Cocyclizations of methylenecyclopropanes with carbon monoxide

(Chemical Equation Presented) Activation of C-C bonds in cyclopropanes with a cobalt complex: Methylenecyclopropanes react with one equivalent of [Co 2(CO)8] under mild conditions to give 2- methylenecyclobutanones in moderate to goo

Ruthenium-catalysed synthesis of chiral exocyclic allylic alcoholsviachemoselective transfer hydrogenation of 2-arylidene cycloalkanones

An exclusive asymmetric reduction of C=O bonds of 2-arylidene four-, five-, six-, and seven-membered cycloalkanones has been studied systematically. The asymmetric transfer hydrogenation was performed using a robust and commercially available chiral diamine-derived ruthenium complex as a catalyst and HCOOH/Et3N as a hydrogen source under mild conditions, giving 51 examples of chiral exocyclic allylic alcohols in up to 96% yield and 99% ee. This method was also applicable to the gram-scale synthesis of the active intermediates of the anti-inflammatory loxoprofen and natural product (?)-goniomitine.

Stereospecific Synthesis of Enantioenriched Alkylidenecyclobutanones via Formal Vinylidene Insertion into Cyclopropanone Equivalents

1-Sulfonylcyclopropanols are employed here as efficient cyclopropanone equivalents in a formal vinylidene insertion process, providing the first general synthetic route to enantioenriched alkylidenecyclobutanones. The addition of an alkenyl-Grignard reage

DFT and experimental studies on Rh(III)-catalyzed dual directing-groups-assisted [3+2] annulation and ring-opening of N?aryloxyacetamides with 1-(phenylethynyl)cycloalkanol

A density functional theory (DFT) has been conducted to elucidate the mechanism of N-aryloxyacetamides reacting with 1-(phenylethynyl)cyclobutanol and 1-(phenylethynyl)cyclopentanol under rhodium (III) catalysis. The impact of substrates with different ri

Diastereoselective and Stereodivergent Synthesis of 2-Cinnamylpyrrolines Enabled by Photoredox-Catalyzed Iminoalkenylation of Alkenes

A photoredox-catalyzed iminoalkenylation of γ-alkenyl O-acyl oximes has been developed. Readily available alkenylboronic acids serve as alkenylation reagents, leading to densely functionalized pyrrolines. Both (E)- and (Z)-cinnamylpyrrolines are accessible depending on the reaction solvent. In dichloromethane, (E)-cinnamylpyrrolines are produced through a photoredox-mediated single-electron-transfer process. In tetrahydrofuran, (Z)-cinnamylpyrrolines are generated by photocatalytic contra-thermodynamic E-to-Z isomerization of (E)-cinnamylpyrrolines though an energy-transfer pathway. Two stereocenters are established with complete diastereoselectivity and only one diastereomer is isolated.

Gold(I)-Catalyzed Ring Expansion of Alkynylcyclopropyl Allyl Ethers to Construct Tetrasubstituted Methylenecyclobutanones: A Mechanistic Investigation about the Character of Catalytic Amount of Water

A gold(I)-catalyzed ring expansion of alkynylcyclopropyl allyl ethers to produce tetrasubstituted methylenecyclobutanones in moderate to good yields has been disclosed in this paper. This reaction proceeded through an intramolecular [3,3]-sigmatropic rearrangement followed by [1,2]-allyl shift pathway in the presence of catalytic amount of water upon gold(I) catalysis. The intriguing reaction mechanism has been proposed on the basis of deuterium and 18O-labeling experiments, Mass spectroscopic analysis, 1H and 13C nuclear magnetic resonance (NMR) spectroscopic tracking and density functional theory (DFT) calculations. The further transformation of these methylenecyclobutanones into polycyclic skeleton has been realized by a practical three-step synthetic procedure. Several other transformations have been also indicated. (Figure presented.).

Selective Asymmetric Hydrogenation of Four-Membered Exo-α,β-Unsaturated Cyclobutanones Using RuPHOX-Ru as a Catalyst

The selective asymmetric hydrogenation of four-membered exo-α,β-unsaturated cyclobutanones has been achieved for the first time using RuPHOX-Ru as a catalyst, providing four-membered exo-cyclic chiral allylic alcohols in high yields and with up to 99.9% e

Rhodium(I)-Catalyzed [4 + 2] Cycloaddition Reactions of 2-Alkylenecyclo-butanols with Alkynes and (E)-2-Nitroethenylbenzene through C(sp2)—C(sp3) Bond Cleavage

An intermolecular [4 + 2] cycloaddition was realized through C—C bond cleavage in the presence of Rh(I) catalyst. The selective ring opening of 2-alkylenecyclobutanols enables the generation of active alkenylrhodium species, which underwent smooth cross addition over alkynes and (E)-2-nitroethenylbenzene, leading to highly substituted all-carbon six-membered rings in a single step and in a complete atom economy.

Radical-induced ring-opening and reconstruction of cyclobutanone oxime esters

The first example of intramolecular ring-opening and reconstruction of cyclobutanone oxime esters via selective C-C bond cleavage leading to the synthesis of 3,4-dihydronaphthalene-2-carbonitriles in the presence of a cheap copper catalyst has been reported. The protocol is distinguished by mild and safe reaction conditions that exclude ligands, oxidants, bases, toxic cyanide salts and tolerates a wide scope of cyclobutanones without compromising their efficiency and scalability. The alternative visible-light-driven photoredox process for this coupling reaction was also uncovered.

Rh(I)-catalyzed ring-opening of cyclobutanols via C–C bond activation: Synthesis of cis-olefin with a remote aldehyde

A Rh(I)-catalyzed ring-opening of cyclobutanols has been developed with ring opening products bearing cis-olefin and a remote aldehyde. Various substrates bearing different substituted aryl groups, heterocyclic groups and alkyl groups were compatible with