Catalyst-free alkanoylation of aromatic rings via arylstannanes. Scope and limitations

The reaction of alkanoyl chlorides with arylstannanes in 1,2-dichlorobenzene (180 °C) is a simple and direct route for the catalyst-free and regioselective synthesis of tertiary alkyl aryl ketones in good to excellent isolated yields (55–77%). Nevertheless, under similar conditions, reactions carried out with alkanoyl chlorides bearing α-hydrogens render only the product of protodestannylation.

Graphical abstractTertiary alkanoyl chlorides react regioselectively with electronically diverse arylstannanes to form the corresponding aryl ketones in good to excellent yields in absence of any type of catalyst. Under these conditions acid chlorides bearing α-hydrogens render only protodestannylation products.Figure optionsDownload full-size imageDownload as PowerPoint slide