An efficient regioselective protocol for the C-C bond formation by the unexpected α,α-diarylation of aromatic ketones with unactivated arenes in the presence of selenium dioxide and boron trifluoride etherate has been developed. The generality and functional tolerance of this protocol is demonstrated by the synthesis of a series of triarylethanones.
The oxidative coupling of the α‐carbon atom of aromatic ketones with unactivated arenes in the presence of selenium dioxide and p‐toluenesulfonic acid monohydrate is described. A number of unsymmetrical benzils have been prepared in good yields (38–75 %) with high regioselectivity. The generality and functional tolerance of this new protocol is demonstrated. The mechanistic pathway for the oxidative coupling reaction is also described. The reaction displays superiority in terms of minimization of steps with the C–C bond formation promoted by SeO2 and pTsOH·H2O. This method is advantageous as the reactants used as the solvent can be recovered.
KF-Al 2 O 3 as a recyclable basic catalyst for the three-component synthesis of 4H-pyran derivatives by the reaction of aldehydes, malononitrile and active methylene dicarbonyl compounds in ethanol at room temperature is described. The protocol is environmentally benign and offers rapid access to a wide array of 4H-pyran heterocycles in good to excellent yields. F
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