Mechanochemical Defluorinative Arylation of Trifluoroacetamides: An Entry to Aromatic Amides
Satenik Mkrtchyan, Mohanad Shkoor, Mandalaparthi Phanindrudu, Miroslav Medveď, Olena Sevastyanova, Viktor O. Iaroshenko
Abstract
High Resolution Image Download MS PowerPoint Slide The amide bond is prominent in natural and synthetic organic molecules endowed with activity in various fields. Among a wide array of amide synthetic methods, substitution on a pre-existing (O)C–N moiety is an underexplored strategy for the synthesis of amides. In this work, we disclose a new protocol for the defluorinative arylation of aliphatic and aromatic trifluoroacetamides yielding aromatic amides. The mechanochemically induced reaction of either arylboronic acids, trimethoxyphenylsilanes, diaryliodonium salts, or dimethyl(phenyl)sulfonium salts with trifluoroacetamides affords substituted aromatic amides in good to excellent yields. These nickel-catalyzed reactions are enabled by C–CF 3 bond activation using Dy 2 O 3 as an additive. The current protocol provides versatile and scalable routes for accessing a wide variety of substituted aromatic amides. Moreover, the protocol described in this work overcomes the drawbacks and limitations in the previously reported methods.