14919-06-3

Upstream product

• 2719-27-9 cyclohexanylcarbonyl chloride 
• 917-64-6 methyl magnesium iodide 
• 90542-25-9 Bis-(1,2-dimethyl-propyl)-((Z)-1-iodo-oct-1-enyl)-borane 
• 87393-83-7 ((Z)-1-Bromo-oct-1-enyl)-dicyclohexyl-borane 
• 87393-84-8 Dicyclohexyl-((Z)-1-iodo-oct-1-enyl)-borane 
• 108-85-0 1-bromocyclohexane 
• 124-13-0 Octanal 
• 68571-10-8 cyclohexyl(pyrrolidin-1-yl)methanone 
• 21369-64-2 n-hexyllithium 

Relevant academic research and scientific papers

A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects

We report that the nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides by organolithium reagents proceeds quickly (20 s reaction time), efficiently, and chemoselectively with a broad substrate scope in the environmentally responsible cyclopentyl methyl ether, at ambient temperature and under air, to provide ketones in up to 93 % yield with an effective suppression of the notorious over-addition reaction. Detailed DFT calculations and NMR investigations support the experimental results. The described methodology was proven to be amenable to scale-up and recyclability protocols. Contrasting classical procedures carried out under inert atmospheres, this work lays the foundation for a profound paradigm shift of the reactivity of carboxylic acid amides with organolithiums, with ketones being straightforwardly obtained by simply combining the reagents under aerobic conditions and with no need of using previously modified or pre-activated amides, as recommended.

Practical one-pot preparation of ketones from aryl and alkyl bromides with aldehydes and DIH via Grignard reagents

Various diaryl ketones, alkyl aryl ketones, and dialkyl ketones were efficiently prepared in good yields by the reactions of the Grignard reagents derived from aryl or alkyl bromides, followed by the reactions with aromatic or aliphatic aldehydes and the subsequent treatment with 1,3-diiodo-5,5- dimethylhydantoin and K2CO3, in a one-pot method. The same treatment of aromatic bromides bearing electron-withdrawing groups, such as ester, nitrile, ketone, and nitro groups with i-PrMgCl·LiCl or PhMgCl instead of Mg, also provided the corresponding diaryl and alkyl aryl ketones in good yields. The above methods are simple and practical transition-metal-free methods for the preparation of various diaryl ketones and alkyl aryl ketones bearing electron-rich aromatic groups and electron-deficient aromatic groups, as well as dialkyl ketones.

NOVEL SYNTHESIS OF INTERNAL ALKENYLDIALKYLBORANE BY THE REACTION OF 1-HALO-1-ALKENYLDIALKYLBORANE WITH GRIGNARD REAGENT.

To synthesize internal alkenyldialkylboranes, coupling reactions were carried out by using 1-halo-1-alkenyldialkylboranes and Grignard reagents. Hydrogen peroxide oxidation and protonolysis with acetic acid of the reaction product revealed that internal (E)-alkenyldialkylborane was formed in 60-90% yield.