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Relevant academic research and scientific papers

Heterogeneously catalyzed direct cross-coupling of secondary alcohols to β-disubstituted ketones by Cu/γ-Al2O3

This study describes the development of Cu/γ-Al2O3 heterogeneously catalyzed cross-coupling of secondary alcohols reaction in the construction of β-disubstituted ketones. Noteworthy, the study reports for the first time, the application of a heterogeneous catalyst in the direct cross-coupling of secondary alcohols. Mechanistic investigations indicate that the activation of alcohols via the cooperation of Cu and γ-Al2O3 plays a crucial role in cross-coupling reactions. This reaction exhibited good substrate compatibility, and the catalyst exhibited constant efficiency even after five reaction cycles. This novel methodology can be applied as a powerful, low-cost, and safe technology for the construction of β-disubstituted ketones.

C-C coupling of ketones with methanol catalyzed by a N-heterocyclic carbene-phosphine iridium complex

An N-heterocyclic carbene-phosphine iridium complex system was found to be a very efficient catalyst for the methylation of ketone via a hydrogen transfer reaction. Mild conditions together with low catalyst loading (1 mol%) were used for a tandem process which involves the dehydrogenation of methanol, C=C bond formation with a ketone, and hydrogenation of the new generated double bond by iridium hydride to give the alkylated product. Using this iridium catalyst system, a number of branched ketones were synthesized with good to excellent conversions and yields.

Reductive alkylation of electronegatively-substituted alkenes by alkylmercury halides

Photolysis of alkylmercury halides in the presence of electronegatively-substituted 1-alkenes yields adduct radicals [RCH2CH(EWG).] that in some cases react with RHgX to form RCH2CH(HgX)(EWG), e.g., EWG = (EtO)2PO or PhSO2. When the EWG is carbonyl or cyano, the resonance stabilized adduct radicals fail to react with the alkyl mercury halide. In these cases photolysis with RHgCl/KI in Me2SO leads to the adduct mercurial via reaction of the adduct radicals with RHgI2-. The reactions of tertiary-enolyl adduct radicals are inefficient with RHgX/KI, and disproportionation of the adduct radicals is the major reaction pathway. For secondary- or tertiary-adduct radicals the reductive alkylation products are formed in excellent yield by reaction with RHgCl and silyl hydrides in Me2SO solution in a process postulated to involve RHgH as an intermediate. The relative reactivities of a number of α,β-unsaturated systems toward t-Bu. have been measured by competitive techniques. The results demonstrate a high reactivity of s-cis enones relative to the s-trans conformers.