573671-27-9

Upstream product

• 274-09-9 Methylenedioxybenzene 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 
• 446065-11-8 cyclohexyltrifluoro-λ⁴-borane potassium salt 
• 4441-56-9 cyclohexylboronic acid 
• 126812-30-4 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate 
• 120-57-0 piperonal 
• 28075-50-5 cyclohex-1-en-1-yl trifluoromethane sulfonate 
• 120-80-9 benzene-1,2-diol 

Downstream Products

• 573671-29-1 2-[1-Benzo[1,3]dioxol-5-yl-1-cyclohexyl-meth-(Z)-ylidene]-succinic acid 
• 573671-34-8 3-(benzo[1,3]dioxol-5-yl-cyclohexyl-methyl)-dihydro-furan-2,5-dione 

Relevant academic research and scientific papers

Synergistic Photoredox/Nickel Coupling of Acyl Chlorides with Secondary Alkyltrifluoroborates: Dialkyl Ketone Synthesis

Visible light photoredox/nickel dual catalysis has been employed in the cross-coupling of acyl chlorides with potassium alkyltrifluoroborates. This protocol, based on single-electron-mediated alkyl transfer, circumvents the restriction of using reactive alkylmetallic nucleophiles in transition-metal-catalyzed acylation and achieves a mild and efficient method for the synthesis of unsymmetrical alkyl ketones. In this approach, a variety of acyl chlorides have been successfully coupled with structurally diverse potassium alkyltrifluoroborates, generating the corresponding ketones with good yields.

Nickel-Mediated Photoreductive Cross Coupling of Carboxylic Acid Derivatives for Ketone Synthesis**

A simple visible light photochemical, nickel-catalyzed synthesis of ketones from carboxylic acid-derived precursors is presented. Hantzsch ester (HE) functions as a cheap, green and strong photoreductant to facilitate radical generation and also engages in the Ni-catalytic cycle to restore the reactive species. With this dual role, HE allows for the coupling of a large variety of radicals (1°,2°, benzylic, α-oxy & α-amino) with aroyl and alkanoyl moieties, a new feature in reactions of this type. With both precursors deriving from abundant carboxylic acids, this protocol is a welcome addition to the organic chemistry toolbox. The reaction proceeds under mild conditions without the need for toxic metal reagents or bases and shows a wide scope, including pharmaceuticals and complex molecular architectures.

Vinyl Triflate–Aldehyde Reductive Coupling–Redox Isomerization Mediated by Formate: Rhodium-Catalyzed Ketone Synthesis in the Absence of Stoichiometric Metals

Direct conversion of aldehydes to ketones is achieved via rhodium-catalyzed vinyl triflate-aldehyde reductive coupling-redox isomerization mediated by potassium formate. This method circumvents premetalated C-nucleophiles and discrete redox manipulations typically required to form ketones from aldehydes.

Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N-C Cleavage of Imides

An electrophilic, imide-based, visible-light-promoted photoredox/Ni-catalyzed cross-coupling reaction for the synthesis of aliphatic ketones has been developed. This protocol proceeds through N-C(O) bond activation, made possible through the lower activation energy for metal insertion into this bond due to delocalization of the lone pair of electrons on the nitrogen by electron-withdrawing groups. The operationally simple and mild cross-coupling reaction is performed at ambient temperature and exhibits tolerance for a variety of functional groups.

Tetralone acids as intermediates for the synthesis of podophyllotoxin analogues

Tetralone acids 6, 7 and 8 have been synthesised as intermediates for the synthesis of podophyllotoxin analogues 3, 4 and 5. The possible steric hindrance of cyclohexyl group on the intramolecular Friedel-Crafts acylation reaction of anhydrides 15 b,c to tetralone acids 7 and 8 is also discussed here.