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Relevant academic research and scientific papers

InI3/me3sii-catalyzed direct alkylation of enol acetates using alkyl acetates or alkyl ethers

A combined Lewis acid of InI3 and Me3SiI was used to catalyze the direct coupling reactions of enol acetates with alkyl acetates or alkyl ethers without generating metal waste. The easily-handled alkylating reagents enlarged the application area of this coupling reaction. 2011 The Chemical Society of Japan.

InCl3/Me3SiBr-catalyzed direct coupling between silyl ethers and enol acetates

A combined Lewis acid catalyst of InCl3 and Me3SiBr promoted the direct use of enol acetates in the coupling with low-reactive silyl ethers, in which functional groups including ketones and aldehydes survived. Sterically hindered silyl ethers such as ROSiEt3, ROSiPh3, ROSit-BuMe2, and ROSii-Pr3 were also applicable.

α-Alkylation of carbonyl compounds by direct addition of alcohols to Enol acetates

A practical α-alkylation of ketones and aldehydes has been achieved by the direct addition of alcohols to enol acetates. The moderate Lewis acidity of InI3, CaBr3, and FeBr3 is a key factor in the catalytic cycle, and many different alcohols and enol acetates have been successfully used in this procedure.

Indium-catalyzed coupling reaction between silyl enolates and alkyl chlorides or alkyl ethers

The coupling reactions of alkyl chlorides with silyl enolates catalyzed by InBr3, and the coupling reactions of alkyl ethers with silyl enolates catalyzed by the combined Lewis acid of InBr3/Me3SiBr are described. In both reaction systems, various types of silyl enolates were used to give corresponding α-alkylated esters, ketones, carboxylic acids, amides, thioesters, and aldehydes.

α-alkylation of ketones by addition of zinc enamides to unactivated olefins

A zinc enamide generated from the corresponding N-aryl imine undergoes addition to an unactivated olefin, such as ethylene, 1-octene, and isobutylene, to generate an α-alkylated γ-zincioimine intermediate in good to excellent yield. Terminal and gem-disubstituted olefins react with >99% regioselectivity, allowing the C-C bond formation to take place at the more hindered carbon of the double bond. The organozinc intermediate undergoes further C-C bond formation with a carbon electrophile to give, upon hydrolysis of the imine, an α-alkylated ketone bearing a variety of functionalized primary, secondary, and tertiary alkyl groups.

Regioselective Lewis Acid-mediated α-sec-Alkylation of Carbonyl Compounds

Carbonyl compounds such as ketones, aldehydes, acyloins, or carboxylic esters can be alkylated at the α-position via the corresponding O-silylated forms using activated alkyl halides or acetates in the presence of Lewis acids.In the case of unsymmetricall