Direct α-alkylation of unactivated ketones using benzylic alcohols as electrophiles has been achieved at room temperature. This reaction takes place via in situ formed acetal using triflic acid and trimethyl orthoformate. It is believed that methyl vinyl ether formed from the in situ generated dimethyl acetal in the presence of triflic acid undergoes alkylation. Diverse ketones could be alkylated with diarylmethanols, cinnamyl alcohols, and phenyl propargyl alcohols having different electrophilicities.
A mild chemoselective method for S-arylation of cysteine has been developed in an open-flask procedure under metal-free conditions using arenediazonium salts in methanol.
A practically simple and direct a-alkylation of unactivated ketones using benzylic alcohols has been achieved. The in situ formed acetals are the key for the success of the reaction. The catalyst, silver hexafluoroantimonate(V) (AgSbF 6 ) provides double activation by converting the ketone into an enol ether via acetal and generation of carbocationic center at the benzylic position of the benzylic alcohol. The alcohols include benzylic propargyl alcohols, cinnamyl alcohols, and diarylmethanols.
Here we describe a facile, tandem synthetic route for β-carbolinones, a class of natural products of high biological significance. Commercially available building blocks yield highly diverse analogues in just two simple steps.
Tertiary propargyl alcohols undergo smooth Meyer-Schuster rearrangement to give enones in the presence of silver catalyst alone at room temperature. The intermediate can be trapped using NIS to make useful tetra substituted α-iodoenones.
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