60148-00-7

Upstream product

• 70423-46-0 α-Cyclohexyl-3-pyridinmethanol 
• 59020-09-6 3-(trimethylstannyl)pyridine 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 2043-61-0 cyclohexanecarbaldehyde 
• 626-55-1 3-Bromopyridine 
• 220565-63-9 pyridin-3-ylzinc(II) bromide 
• 1120-90-7 3-iodopyridine 
• 500-22-1 3-pyridinecarboxaldehyde 
• 17566-51-7 N,N-dimethylcyclohexanecarboxamide 
• 100-54-9 pyridine-3-carbonitrile 

Downstream Products

• 87149-28-8 α-Cyclohexyl-α-trichlormethyl-3-pyridinmethanol 
• 749255-12-7 3-(2-cyclohexyloxiran-2-yl)pyridine 
• 790691-17-7 1-cyclohexyl-1-(3-pyridyl)-2-(1,2,4-triazol-1-yl)ethanol 
• 1361052-25-6 C₁₈H₁₄F₅NO 
• 70423-46-0 α-Cyclohexyl-3-pyridinmethanol 

Relevant academic research and scientific papers

Direct C-H Arylation of Aldehydes by Merging Photocatalyzed Hydrogen Atom Transfer with Palladium Catalysis

Herein, we report that merging palladium catalysis with hydrogen atom transfer (HAT) photocatalysis enabled direct arylations and alkenylations of aldehyde C-H bonds, facilitating visible light-catalyzed construction of a variety of ketones. Tetrabutylammonium decatungstate and anthraquinone were found to act as synergistic HAT photocatalysts. Density functional theory calculations suggested a Pd0-PdII-PdIII-PdI-Pd0 pathway and revealed that regeneration of the Pd0 catalyst and the photocatalyst occurs simultaneously in the presence of KHCO3. This regeneration features a low energy barrier, promoting efficient coupling of the palladium catalytic cycle with the photocatalytic cycle. The work reported herein suggests great promise for further applications of HAT photocatalysis in palladium-catalyzed cross-coupling and C-H functionalization reactions to be successful.

Double duty for cyanogen bromide in a cascade synthesis of cyanoepoxides

An unprecedented reaction mode of cyanogen bromide has been discovered. Under basic conditions, cyanogen bromide acts as an equivalent of both Br + and CN- to convert enolizable ketones into the corresponding cyanoepoxides in good yields. This unique reaction mode provides new, one-pot access to densely substituted cyanoepoxides from easily available ketones (see scheme). Copyright

2-Pyridyl and 3-pyridylzinc bromides: direct preparation and coupling reaction

A facile synthetic approach to the direct preparation of 2-pyridyl and 3-pyridylzinc bromides has been demonstrated using Rieke zinc with 2-bromopyridine and 3-bromopyridine, respectively. A variety of different electrophiles have been coupled with the resulting organozinc reagents to give the corresponding cross-coupling products in moderate to good yields.

A facile synthetic approach to the preparation of 3-pyridyl derivatives: Preparations and coupling reactions of 3-pyridylzinc and its analogues

A facile synthetic approach to the direct preparation of 3pyridylzinc bromide has been demonstrated using Rieke zinc with 3-bromopyridine in the presence of a catalytic amount of lithium chloride. A variety of different electrophiles have been coupled to give the corresponding cross-coupling products in moderate to good yields. Also, this methodology has been expanded to the preparation of the corresponding organozinc reagents of 3-bromopyridine analogues. Georg Thieme Verlag Stuttgart.

Palladium-catalyzed synthesis of aryl ketones by coupling of aryl bromides with an acyl anion equivalent

Palladium-catalyzed couplings of aryl bromides with N-tert-butylhydrazones as acyl anion equivalents to form aryl ketones are reported. The coupling process occurs at the C-position of hydrazones to form N-tert-butyl azo compounds. Isomerization of these azo compounds to the corresponding hydrazones, followed by hydrolysis, gave the desired mixed alkyl aryl ketones. The selectivity of C- versus N-arylation was strongly influenced by the substituent on nitrogen. Arylation at carbon occurred with N-tert-butylhydrazones, whereas N-arylation occurred with N-arylhydrazones. The arylation of hydrazones containing primary and secondary alkyl groups, as well as aryl groups, gave the desired ketones in good yields after hydrolysis. Functional groups on the aromatic ring, such as alkoxy, cyano, trifluoromethyl, carboalkoxy, carbamoyl, and keto groups, were tolerated. This reaction likely occurs by C-C bond-forming reductive elimination from an intermediate containing an η1-diazaallyl ligand. Copyright

Synthesis of substituted 2-azolyl-1-pyridylethan-1-ols

Through the reaction of (2-aryloxiran-2-yl)pyridines with triazole or imidazole a series of novel 2-azolyl-1-pyridylethan-1-ols has been synthesized with different positioning of the nitrogen atom in the pyridine fragment for pharmacological and agrochemi

Fungicidal Pyridine Derivatives I: α-Trichloromethyl-3-pyridinemethanols

The title substances, a new type of compounds with fungicidal activity, were synthesized by addition of trichloromethyllithium (and tribromomethyllithium resp.) to various 3-pyridyl ketones at -100 deg C. - Keywords: Fungicides; Pyridinemethanoles; Trichl

A New Simple Synthesis of Fusaric Acid and Other 5-Alkyl-2-pyridinecarboxylic Acids

Carboxamido groups are introduced into the 6-position of 3-acylpyridines with high regioselectivity via Minisci reaction with formamides, Fe(II) sulfate and tert-butyl hydroperoxide.The isolation procedure is considerably improved by the addition of citric acid for complexation of the Fe ions.Fusaric acid and other 5-alkyl-2-pyridine carboxylic acids are obtained by a following Wolff-Kishner reaction in 20-75percent overall yield.

A SIMPLE METHOD FOR INTRODUCTION OF ACYL GROUPS INTO PYRIDINE NUCLEI VIA TRIMETHYLSTANNYL-PYRIDINES AND QUINOLINES.

The 2-trimethylstannyl (TMSn) derivatives of pyridine and quinoline were directly treated with acyl chlorides to afford the corresponding 2-acyl-pyridines and -quinolines in good yields.On the other hand, replacement of the 3- and 4-TMSn groups by acyl groups was satisfactorily achieved by catalysis of palladium compound such as PdCl2 or PdCl2(PPh3)2.

Studies on Organometallic Compounds. III. Reaction of Trimethylstannylazines with Acyl Chlorides. A Novel C-C Bond Formation of Pyridine Nuclei

Introduction of an acyl group at the α-, β-, and γ-positions of pyridine nuclei was accomplished. 2-Trimethylstannyl-pyridine and -quinoline and 1-trimethylstannylisoquinoline directly reacted with various acyl chlorides to give the corresponding 2-pyridyl, 2-quinolyl, and 1-isoquinolyl ketones, respectively.Reaction of 3-trimethylstannylpyridine, -quinoline, and -isoquinoline with acyl chlorides proceeded smoothly under catalysis by PdCl2 or PdCl2(PPh3)2 to afford the corresponding ketones in good yields.Similary, 4-pyridyl, -quinolyl, and -isoquinolyl ketones were prepared from corresponding 4-trimethylstannyl derivatives and acyl chlorides.Keywords--trimethylstannylazine; palladium-catalyzed reaction; acylation; palladium dichloride; dichlorobis(triphenylphosphine)palladium(II)