5685-43-8

Upstream product

• 5722-11-2 rac-2,2-dimethylcyclopropanecarbonitrile 
• 49675-52-7 (5,5-dimethyl-5H-pyrazol-3-yl)-phenyl-methanone 
• 118526-90-2 (2,2-Dimethyl-cyclopropaneselenonyl)-benzene 
• 100-52-7 benzaldehyde 
• 95323-09-4 (2,2-Dimethyl-cyclopropylselanyl)-benzene 
• 75-11-6 diiodomethane 
• 5650-07-7 3-methyl-1-phenyl-but-2-en-1-one 
• 70775-39-2 dimethylsulfoxonium methylide 
• 95465-44-4 3-methyl-1-phenylbut-2-en-1-ol 
• 1774-47-6 trimethylsulfoxonium iodide 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 100-58-3 phenylmagnesium bromide 
• 38614-36-7 2-methylpropen-1-ylmagnesium bromide 

Downstream Products

• 104722-68-1 1-(1-benzoyl-2,2-dimethylcyclopropyl) 2-benzoyl-2-propylselenide 
• 77070-50-9 4-Iodo-4-methyl-1-phenyl-pentan-1-one 
• 127793-52-6 (2,2-Dimethyl-cyclopropyl)-[4-(4-hydroxy-1,1-dimethyl-4-phenyl-butyl)-phenyl]-methanone 
• 138354-17-3 (2,2-Dimethyl-cyclopropyl)-(4-{4-hydroxy-4-[4-(4-hydroxy-1,1-dimethyl-4-phenyl-butyl)-phenyl]-1,1-dimethyl-butyl}-phenyl)-methanone 
• 138354-18-4 (2,2-Dimethyl-cyclopropyl)-{4-[4-hydroxy-4-(4-{4-hydroxy-4-[4-(4-hydroxy-1,1-dimethyl-4-phenyl-butyl)-phenyl]-1,1-dimethyl-butyl}-phenyl)-1,1-dimethyl-butyl]-phenyl}-methanone 
• 36939-18-1 (2,2-Dimethyl-cyclopropylmethyl)-benzene 
• 104722-76-1 C₂₂H₂₄O₃Se 
• 104722-71-6 bis-1-(1-benzoyl-2,2-dimethylcyclopropane) diselenide 
• 104722-79-4 C₂₄H₂₆O₃Se₂ 

Relevant academic research and scientific papers

SmI2-Catalyzed Intermolecular Coupling of Cyclopropyl Ketones and Alkynes: A Link between Ketone Conformation and Reactivity

The archetypal single electron transfer reductant, samarium(II) diiodide (SmI2, Kagan's reagent), remains one of the most important reducing agents and mediators of radical chemistry after four decades of widespread use in synthesis. While the chemistry of SmI2 is very often unique, and thus the reagent is indispensable, it is almost invariably used in superstoichiometric amounts, thus raising issues of cost and waste. Of the few reports of the use of catalytic SmI2, all require the use of superstoichiometric amounts of a metal coreductant to regenerate Sm(II). Here, we describe a SmI2-catalyzed intermolecular radical coupling of aryl cyclopropyl ketones and alkynes. The process shows broad substrate scope and delivers a library of decorated cyclopentenes with loadings of SmI2 as low as 15 mol %. The radical relay strategy negates the need for a superstoichiometric coreductant and additives to regenerate SmI2. Crucially, our study uncovers an intriguing link between ketone conformation and efficient cross-coupling and thus provides an insight into the mechanism of radical relays involving SmI2. The study lays further groundwork for the future use of the classical reagent SmI2 in contemporary radical catalysis.

Hantzsch Ester-Mediated Photochemical Transformations in the Ketone Series: Remote C(sp3)-H Arylation and Cyclopentene Synthesis through Strain Release

A metal-free Hantzsch ester-mediated synthesis of cyclopentenylketones as well as O-hetarylketones starting from ketocyclopropanes under eco-friendly conditions was developed. The versatility of the developed conditions is shown by reacting ketocyclopropanes in both a formal [3 + 2] cycloaddition with terminal alkynes (further investigated using theoretical calculations) and a radical C-C-coupling with cyanopyridines. The newly developed methodologies were later on utilized as a downstream reaction for photogenerated cyclopropanes combining UV and visible light photochemistry. Following this procedure, a UV-driven Norrish-Yang-type reaction induces the ring strain of the intermediates, which serves as activation energy for the subsequent ring transformation.

A General Protocol for Radical Anion [3+2] Cycloaddition Enabled by Tandem Lewis Acid Photoredox Catalysis

A method for intermolecular [3+2] cycloaddition between aryl cyclopropyl ketones and alkenes involving the combination of Lewis acid and photoredox catalysis is reported. In contrast to other more common methods for [3+2] cycloaddition, these conditions o

Diastereo- and Enantioselective Formal [3 + 2] Cycloaddition of Cyclopropyl Ketones and Alkenes via Ti-Catalyzed Radical Redox Relay

We report a stereoselective formal [3 + 2] cycloaddition of cyclopropyl ketones and radical-acceptor alkenes to form polysubstituted cyclopentane derivatives. Catalyzed by a chiral Ti(salen) complex, the cycloaddition occurs via a radical redox-relay mechanism and constructs two C-C bonds and two contiguous stereogenic centers with generally excellent diastereo- and enantioselectivity.

Enantioselective Photocatalytic [3 + 2] Cycloadditions of Aryl Cyclopropyl Ketones

Control of stereochemistry in photocycloaddition reactions remains a substantial challenge; almost all successful catalytic examples to date have involved [2 + 2] photocycloadditions of enones. We report a method for the asymmetric [3 + 2] photocycloaddition of aryl cyclopropyl ketones that enables the enantiocontrolled construction of densely substituted cyclopentane structures not synthetically accessible using other catalytic methods. These results show that the dual-catalyst strategy developed in our laboratory broadens synthetic chemists' access to classes of photochemical cycloadditions that have not previously been feasible in enantioselective form.

Nickel-catalysed cyclopropanation of electron-deficient alkenes with diiodomethane and diethylzinc

In the presence of a nickel catalyst, the cyclopropanation of electron-deficient alkenes with diiodomethane and diethylzinc is drastically accelerated. A wide range of cyclopropyl ketones, esters and amides can be accessed under these conditions.

EXPLORATORY STUDY ON α-METALLO SELENONES : Original Syntheses of Oxaspiropentanes.

Oxaspiropentanes have been obtained from α-metallocyclopropyl phenyl selenones and carbonyl compounds and on reaction of a base with β-hydroxyalkyl cyclopropyl selenones.The original reactivity of other β-hydroxyalkyl selenones is also disclosed.