Synthesis of α-benzylated amides via electrocatalytic Favorskii rearrangement of 1, 3-diarylacetones

Add time:07/24/2019    Source:sciencedirect.com

Electrolysis of 1,3-diarylacetones with aliphatic amines in Bu4NI/CH3CN to racemic Favorskii amides via benzyl group rearrangement has been developed. The electroconversion is easily conducted in a simple undivided cell under constant-current conditions at room temperature. The electrocatalytic Favorskii rearrangement of 1,3-diarylacetones including electron-withdrawing substituents was favored and gave a good yield of α-benzylated amides. When several unsymmetrical ketones were employed as substrates, this rearrangement with moderate regioselectivity was observed. This chemistry also provides an efficient approach to construct a chiral center at α-position of amides.

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