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InChI:InChI=1/C16H22O2/c1-18-15-10-7-13(8-11-15)9-12-16(17)14-5-3-2-4-6-14/h7-8,10-11,14H,2-6,9,12H2,1H3

Upstream product

• 5720-07-0 4-methoxyphenylboronic acid 
• 112650-62-1 1-cyclohexylcyclopropan-1-ol 
• 110-82-7 cyclohexane 
• 15893-42-2 3-(4-methoxyphenyl)propionyl chloride 
• 108-91-8 cyclohexylamine 
• 1929-29-9 3-(4-methoxyphenyl)propanoic acid 
• 823-76-7 Cyclohexyl methyl ketone 
• 105-13-5 4-Methoxybenzyl alcohol 

Relevant academic research and scientific papers

KETONE SYNTHESIS AND APPLICATIONS

Provided are new nickel./zirconium-mediated coupling reactions useful in the synthesis of ketone-containing compounds, e.g., halichondrin natural products and related molecules. A feature of the present disclosure is the use of a nickel(I) catalyst in tandem with a nickel (II) catalyst in the Ni/Zr-mediated coupling reactions. Without wishing to be bound by any particular theory, the nickel (I) catalyst selectively activates the electrophilic coupling partner (i.e., the compound of Formula (A)), and the nickel(ll) catalyst selectively activates the nucleophilic coupling partner (i.e., a thioester of Formula (B)). This dual catalyst system leads to improved coupling efficiency and eliminates the need for a large excess of one of the coupling partners (i.e., a compound of Formula (A) or (B)).

Nickel-Catalyzed Cross-Coupling of Alkyl Carboxylic Acid Derivatives with Pyridinium Salts via C-N Bond Cleavage

The electrophile-electrophile cross-coupling of carboxylic acid derivatives and alkylpyridinium salts via C-N bond cleavage is developed. The method is distinguished by its simplicity and steers us through a variety of functionalized ketones in good to excellent yields. Besides acid chlorides, carboxylic acids were also employed as acylating agents, which enabled us to incorporate acid-sensitive functional groups such as MOM, BOC, and acetal. Control experiments with TEMPO revealed a radical pathway.

Synergistic Activation of Amides and Hydrocarbons for Direct C(sp3)–H Acylation Enabled by Metallaphotoredox Catalysis

The utilizations of omnipresent, thermodynamically stable amides and aliphatic C(sp3)?H bonds for various functionalizations are ongoing challenges in catalysis. In particular, the direct coupling between the two functional groups has not been realized. Here, we report the synergistic activation of the two challenging bonds, the amide C?N and unactivated aliphatic C(sp3)?H, via metallaphotoredox catalysis to directly acylate aliphatic C?H bonds utilizing amides as stable and readily accessible acyl surrogates. N-acylsuccinimides served as efficient acyl reagents for the streamlined synthesis of synthetically useful ketones from simple C(sp3)?H substrates. Detailed mechanistic investigations using both computational and experimental mechanistic studies were performed to construct a detailed and complete catalytic cycle. The origin of the superior reactivity of the N-acylsuccinimides over other more reactive acyl sources such as acyl chlorides was found to be an uncommon reaction pathway which commences with C?H activation prior to oxidative addition of the acyl substrate.

Utility of Organoboron Reagents in Arylation of Cyclopropanols via Chelated Pd(II) Catalysis: Chemoselective Access to β-Aryl Ketones

Organoborane reagents were investigated as coupling partners to cyclopropanol-derived β-ketone enolates in the presence of a chelated Pd(II) catalyst. Efficient coupling of a range of electronically and sterically diverse cyclopropanols and aryl/alkenyl boronic derivatives (39 examples, 65-94% yield) could be achieved with the generation of synthetically important β-aryl ketone intermediates in a chemoselective fashion. This reactivity paradigm, which broadens the scope of aryl donor partners to homoenolates, allows open-flask conditions, water as a cosolvent, and preparation of halogen-bearing β-aryl ketones that are distinct from previous methods. This chelated Pd(II) catalysis appears to be different from the Pd(0) pathway, as evident from deuterium scrambling studies that could reveal differentiating protonolysis of an α-keto carbopalladium complex in the terminal step.

Development of a convoluted polymeric nanopalladium catalyst: α-alkylation of ketones and ring-opening alkylation of cyclic 1,3-diketones with primary alcohols

A novel solid-phase catalyst of palladium nanoparticles, nano-Pd-V, was prepared from PdCl2 with main-chain viologen polymers via complexation and reduction. This insoluble nanocatalyst nano-Pd-V efficiently promoted α-alkylation of ketones with primary alcohols in the presence of Ba(OH)2·H2O under atmospheric conditions without organic solvents. The nano-Pd-V catalyst was reused without loss of catalytic activity. Ring-opening alkylation of cyclic 1,3-diketones with primary alcohols was also catalyzed by the nano-Pd-V catalyst.

A solid-phase self-organized catalyst of nanopalladium with main-chain viologen polymers: α-alkylation of ketones with primary alcohols

A novel solid-phase self-organized catalyst of palladium nanoparticles was prepared from PdCl2 with main-chain viologen polymers via complexation and reduction. This insoluble nanocatalyst nano-Pd-V efficiently promoted α-alkylation of ketones with primary alcohols in the presence of Ba(OH)2·H2O under atmospheric conditions without organic solvents. The nano-Pd-V catalyst was reused without loss of catalytic activity.