70525-38-1

Upstream product

• 17881-80-0 (2-picolyl)trimethylsilane 
• 1749-19-5 N-(1-phenylethylidene)aniline 
• 110-86-1 pyridine 
• 108-86-1 bromobenzene 
• 52248-74-5 (E)-2-(prop-1-en-1-yl)pyridine 
• 109-06-8 α-picoline 
• 585-71-7 (1-bromoethyl)benzne 
• 98-85-1 1-Phenylethanol 
• 38700-15-1 triphenyl-(2-pyridylmethyl)phosphonium chloride 

Relevant academic research and scientific papers

Aryl-Nickel-Catalyzed Benzylic Dehydrogenation of Electron-Deficient Heteroarenes

This manuscript describes the first practical benzylic dehydrogenation of electron-deficient heteroarenes, including pyridines, pyrazines, pyrimidines, pyridazines, and triazines. This transformation allows for the efficient benzylic oxidation of heteroarenes to afford heterocyclic styrenes by the action of nickel catalysis paired with an unconventional bromothiophene oxidant.

Direct Wittig Olefination of Alcohols

A base-promoted transition metal-free approach to substituted alkenes using alcohols under aerobic conditions using air as the inexpensive and clean oxidant is described. Aldehydes are relatively difficult to handle compared to corresponding alcohols due to their volatility and penchant to polymerize and autoxidize. Wittig ylides are easily oxidized to aldehydes and consequently form homo-olefination products. By the strategy of simultaneously in situ generation of ylides and aldehydes, for the first time, alcohols are directly transferred to olefins with no need of prepreparation of either aldehydes or ylides. Thus, the di/monocontrollable olefination of diols is accomplished. This synthetically practical method has been applied in the gram-scale synthesis of pharmaceuticals, such as DMU-212 and resveratrol from alcohols.

Ruthenium-catalyzed arylation of 2-alkenylpyridines with aryl bromides: Alternative E,Z-selectivity to Mizoroki-Heck reaction

(Chemical Equation Presented) Regio- and stereoselective arylation of 2-alkenylpyridines with aryl bromides is catalyzed by specific Ru(II)-phosphine complexes affording β-arylated (Z)-2-alkenylpyridines, in which the aryl moiety is introduced cis to the

Ruthenium-mediated regio- and stereoselective alkenylation of pyridine

A novel alkenylation reaction of pyridine is developed. Heating a cationic ruthenium vinylidene complex [CpRu(C=C=HR)(PPh3)2]PF6 in pyridine at 100-125 °C for 24 h affords (E)-2-alkenylpyridine. Initially, pyridine coordinates to ruthenium by displacement of one of the phosphine ligands. Then, [2 + 2] heterocycloaddition occurs to form a four-membered ruthenacyclic complex. Deprotonation of the β-hydrogen affords a neutral π-azaallyl complex. Protonolysis furnishes the product. As a result, a vinylidene group is inserted into the α C-H bond of pyridine. The alkenylation reaction is made catalytic in ruthenium by the use of (alkyn-1-yl)silane as the vinylidene source. Treatment of (alkyn-1-yl)trimethylsilane with pyridine in the presence of a cationic ruthenium complex [CpRu(PPh3)2]PF6 affords the corresponding (E)-2-alkenylpyridine in good yield in a regio- and stereoselective manner. Copyright

STEREOSPECIFIC SYNTHESIS OF (E)-ALKENYLPYRIDINES VIA α-SILYL CARBANION

(E)-2-Alkenylpyridines were stereospecifically prepared from 2-(trimethylsilylmethyl)pyridine and the corresponding (E)-aldimines of anilines by an analogous reaction to the Peterson reaction.