35448-12-5

Upstream product

• 54166-92-6 oxalic acid-chloride cyclohexyl ester 
• 79-37-8 oxalyl dichloride 
• 108-93-0 cyclohexanol 

Downstream Products

• 620-82-6 dicyclohexyl oxalate 
• 137634-68-5 1-cyclohexylphthalazine 
• 137655-83-5 methyl 2-cyclohexylisonicotinate 
• 152954-32-0 C₂₂H₂₇IO₈ 
• 83570-32-5 2-chloro-3-cyclohexylnaphthalene-1,4-dione 
• 1040762-49-9 C₂₁H₁₇BrClF₃N₂O₄ 
• 1124-53-4 N-cyclohexylacetamide 
• 26059-80-3 2-cyclohexylquinazolin-4(3Η)-one 
• 16573-53-8 6‐cyclohexylphenanthridine 
• 106662-18-4 methyl 1-cyclohexylisoquinoline-3-carboxylate 
• 33538-11-3 1‐cyclohexylisoquinoline 
• 37597-46-9 4‐cyclohexyl‐2‐methylquinoline 
• 40115-03-5 2-cyclohexyl-benzothiazole 
• 1383708-58-4 1-cyclohexyl-3,4-diphenylisoquinoline 

Relevant academic research and scientific papers

C-H alkylation of heteroarenes with alkyl oxalates by molecular photoelectrocatalysis

An oxidant- and metal-free photoelectrocatalytic C-H alkylation reaction of heteroarenes with alkyl oxalates has been developed. Several classes of heteroaromatics, such as quinolines, isoquinolines, pyridines, and phenanthridines, can be alkylated with t

Metal-, Photocatalyst-, and Light-Free Minisci C-H Alkylation of N-Heteroarenes with Oxalates

Herein, we report a mild protocol for metal-, photocatalyst-, and light-free Minisci C-H alkylation reactions of N-heteroarenes with alkyl oxalates derived from primary, secondary, and tertiary alcohols. The protocol uses environmentally benign persulfate

Hypervalent Iodine(III)-Mediated Decarboxylative Ritter-Type Amination Leading to the Production of α-Tertiary Amine Derivatives

α-Tertiary amines (ATAs) are attractive structural motifs that are frequently found in biologically active molecules. Therefore, the development of an efficient method for the synthesis of ATAs represents an important research topic in the field of medicinal chemistry as well as organic chemistry. Although the Ritter reaction is a reliable approach for preparing α-tertiary amine derivatives via intermolecular amination reactions, the typical methods suffer from disadvantages such as harsh reaction conditions and the use of strong acids. Because of this, it has been of limited use in the synthesis of ATAs. We report here on the decarboxylative Ritter-type amination of carboxylic acids bearing an α-quaternary carbon center using a combination of PhI(OAc)2 and molecular iodine (I2) to produce the corresponding α-tertiary amine derivatives. This reaction proceeded at ambient temperature on the benchtop with a fluorescent light. Mechanistic investigations suggest that the reaction proceeds via the formation of an alkyl iodide and a higher oxidation state iodine(III) species as key intermediates. Similarly, a stepwise protocol for the Ritter-type amination of alcohols via the formation of oxalic acid monoalkyl esters was also achieved. The present methods represent a useful tool for the synthesis of ATAs that are difficult to prepare by conventional methods.

Alcohols as Latent Coupling Fragments for Metallaphotoredox Catalysis: Sp3-sp2 Cross-Coupling of Oxalates with Aryl Halides

Alkyl oxalates, prepared from their corresponding alcohols, are engaged for the first time as carbon radical fragments in metallaphotoredox catalysis. In this report, we demonstrate that alcohols, native organic functional groups, can be readily activated with simple oxalyl chloride to become radical precursors in a net redox-neutral Csp3-Csp2 cross-coupling with a broad range of aryl halides. This alcohol-activation coupling is successfully applied to the functionalization of a naturally occurring steroid and the expedient synthesis of a medicinally relevant drug lead.

Synthesis, crystal structure, and insecticidal activity of novel N-alkyloxyoxalyl derivatives of 2-arylpyrrole

Two series of novel N-alkyloxyoxalyl derivatives of 2-arylpyrrole were synthesized, and their structures were characterized by 1H NMR spectroscopy, elemental analysis, and single-crystal X-ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities, and their insecticidal activities against oriental armyworm, mosquito, and spider mite are comparable to those of the commercialized Chlorfenapyr.

Reductive Addition to Electron-deficient Olefins with Trivalent Iodine Compounds

(Diacyloxyiodo)arene was treated with electron-deficient olefins in the presence of hydrogen donor such as 1,4-cyclohexadiene to give the reductive addition products via alkyl radical through the radical decarboxylative pathway in good yields.Moreover, this system was able to generate either alkoxycarbonyl radicals or alkyl radicals with benzene, which was prepared from alcohol, oxalyl chloride, and (diacetoxyiodo)benzene via two steps, depending on reaction conditions.These radicals were also utilized for C-C bond formation with electron-deficient olefins.

Radical Decarboxylative Alkylation onto Heteroaromatic Bases with Trivalent Iodine Compounds

Heteroaromatic bases containing nitrogen atoms were easily alkylated with carboxylic acids in the presence of benzene and pentafluorobenzene via radical pathways.Similarly, the alkylation onto heteroaromatic bases was carried out with oxalic acid monoalkyl esters, which were prepared from alcohols and oxalyl dichloride, in the presence of the same trivalent iodine compounds.Moreover, this system was applied to the synthesis of C-nucleosides with the carboxylic acids bearing a sugar moiety.

Alkylation of Aromatic Heterocycles with Oxalic Acid Monoalkyl Esters in the Presence of Trivalent Iodine Compounds

Aromatic heterocycles containing nitrogen atoms were easily alkylated with the half esters of oxalic acid, which were prepared from alcohols, in the presence of benzene via radical decarboxylative pathways.This is the first method for the alkylation of aromatic heterocycles with alcohols via the formation of half esters of oxalic acid.