25552-17-4

Upstream product

• 5699-78-5 5-methylhexanoyl chloride 
• 71-43-2 benzene 
• 626-89-1 4-Methyl-1-pentanol 
• 100-47-0 benzonitrile 
• 7429-94-9 isohexylmagnesium bromide 
• 65488-05-3 4-iodobutyrophenone 
• 625-81-0 diisopropyl zinc 
• 645-41-0 triisoamylamine 
• 98-86-2 acetophenone 
• 123-51-3 i-Amyl alcohol 
• 15175-34-5 5-Methyl-1-phenyl-hexen-⁽²⁾-on-⁽¹⁾ 
• 70-11-1 α-bromoacetophenone 
• 590-86-3 isovaleraldehyde 
• 4249-72-3 2-phenoxy-1-phenylethanol 

Downstream Products

• 26307-36-8 2-Benzyl-5-methyl-1-phenyl-hexan-1-on 
• 26307-39-1 5-Methyl-2-(4-methyl-benzyl)-1-phenyl-hexan-1-one 
• 169601-60-9 5,6-dihydro-4-hydroxy-6-(4-methylpentyl)-6-phenyl-2H-pyran-2-one 
• 1436413-30-7 C₂₀H₂₁N 
• 17697-65-3 (5-methyl-hexyl)-benzene 

Relevant academic research and scientific papers

Pd-Catalyzed Redox Divergent Coupling of Ketones with Terpenols

Redox diversity is a common and important feature of nature. Herein, a Pd-catalyzed redox divergent coupling of ketones with terpenols has been developed to access α-substituted ketones with varying degrees of unsaturation. The control of oxidation states of the product is facilitated by employing different additives. With the aid of BnOH as an external hydrogen source, a reductive coupling pathway is thermodynamically favored. The use of LiBr as the additive will reduce the reactivity of Pd-H to divert the selectivity toward α,β-unsatuated ketones. By switching the solvent from toluene to chlorobenzene, the active species Pd-H will be fully quenched to enable oxidative coupling. Gram-scale reaction with lower catalyst loading (0.5 mol %) was also accomplished to highlight the practicability of this protocol. Furthermore, detailed experimental studies were carried out to elucidate the reaction mechanism and the factors enabling manipulation of the redox selectivity. This redox divergent coupling protocol provides an important complement for known precedents on Tsuji-Trost allylation of ketones.

Regioselective Vinylation of Remote Unactivated C(sp3)?H Bonds: Access to Complex Fluoroalkylated Alkenes

Regioselective incorporation of a particular functional group into aliphatic sites by direct activation of unreactive C?H bonds is of great synthetic value. Despite advances in radical-mediated functionalization of C(sp3)?H bonds by a hydrogen-atom transfer process, the site-selective vinylation of remote C(sp3)?H bonds still remains underexplored. Reported herein is a new protocol for the regioselective vinylation of unactivated C(sp3)?H bonds. The remote C(sp3)?H activation is promoted by a C-centered radical instead of the commonly used N and O radicals. The reaction possesses high product diversity and synthetic efficiency, furnishing a plethora of synthetically valuable E alkenes bearing tri-/di-/mono-fluoromethyl and perfluoroalkyl groups.

Mn-Enabled Radical-Based Alkyl-Alkyl Cross-Coupling Reaction from 4-Alkyl-1,4-dihydropyridines

Highly efficient alkylation of β-chloro ketones and their derivatives was achieved by means of domino dehydrochlorination/Mn-enabled radical-based alkyl-alkyl cross-coupling reaction. In situ-generated α,β-unsaturated ketones and their analogues were identified as the reaction intermediates. Known bioactive compounds, such as melperone and azaperone, could be easily prepared from β-chloropropiophenone in two steps.

Photoredox-Catalyzed Decarboxylative Alkylation of Silyl Enol Ethers to Synthesize Functionalized Aryl Alkyl Ketones

Photoredox-catalyzed decarboxylative alkylation of silyl enol ethers has been developed. Diverse functionalized aryl alkyl ketones were afforded in modest to good yields using N-(acyloxy)phthalimide as an easy access alkyl radical source under mild and operationally simple conditions. The excellent performance of drug molecules such as fenbufen and indomethacin and naturally occurring carboxylic acids such as stearic acid and dehydrocholic acid further demonstrated the practicability of the reaction.

Manganese-Catalyzed α-Alkylation of Ketones, Esters, and Amides Using Alcohols

Herein we report the manganese-catalyzed C-C bond-forming reactions via α-alkylation of ketones, amides, and esters, using primary alcohols. β-Alkylation of secondary alcohols by primary alcohols to obtain α-alkylated ketones is also reported. The reactions are catalyzed by a (iPr-PNP)Mn(H)(CO)2 pincer complex under mild conditions in the presence of (catalytic) base liberating water (and H2 in the case of secondary alcohol alkylation) as the sole byproduct.

Synthesis and catalytic applications of ruthenium(ii)-phosphino-oxime complexes

In this work, the preparation of the first ruthenium complexes containing a phosphino-oxime ligand is presented. Thus, the reaction of cis-[RuCl2(DMSO)4] (3) with 2.4 equivalents of 2-Ph2PC6H4CH=NOH (1) in refluxing THF led to the clean formation of the octahedral ruthenium(ii) derivative cis,cis,trans-[RuCl2{κ2-(P,N)-2-Ph2PC6H4CH=NOH}2] (5), whose structure was unambiguously confirmed by means of a single-crystal X-ray diffraction study. Complex 5 could also be synthesized from the reaction of the dimer [{RuCl(μ-Cl)(η6-p-cymene)}2] (4) with an excess of 1 in refluxing toluene. Treatment of 4 with 2 equivalents of 1, in CH2Cl2 at r.t., allowed also the preparation of the half-sandwich Ru(ii) derivative [RuCl{κ2-(P,N)-2-Ph2PC6H4CH=NOH}(η6-p-cymene)][PF6] (6). In addition, complexes 5 and 6 proved to be active catalysts for the rearrangement of aldoximes to primary amides, as well as for the α-alkylation/reduction of acetophenones with primary alcohols, with the former showing the best performances in both processes.

α-alkylation of ketones by trialkylamines under heterogeneous Pd/C catalysis

Ketones are regioselectively α-alkylated with trialkylamines in toluene at 120 °C in the presence of Pd/C.

Dehydrogenative cross-coupling of primary and secondary alcohols

Homo-and cross-coupling of alcohols resulting in the formation of the corresponding ketones in very good to excellent yield was realized through the one-pot sequence of dehydrogenation/ aldol condensation/hydrogenation accompanied by the release of molecular hydrogen. The dehydrogenation and hydrogenation steps are catalyzed by the previously reported ruthernium-and iridiumbased ligand-metal cooperating catalysts.

Deaminative and decarboxylative catalytic alkylation of amino acids with ketones

It cuts two ways: The cationic [Ru-H] complex catalyzes selective coupling of α- and β-amino acids with ketones to form α-alkylated ketone products. The reaction involves C-C and C-N bond cleavage which result in regio- and stereoselective alkylation using amino acids. A broad substrate scope and high functional-group tolerance is demonstrated. Copyright