Selective Conversion of Unactivated C–N Amide Bond to C–C bond via Steric and Electronic Resonance Destabilization

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The chemo- and site-selective reaction at the particular C-N amide bond among a sea of other amides is a significant and long-standing challenge. Although the use of twisted amides has been demonstrated for modifications of inert C-N amide bonds, none of these methods can selectively activate a particular amide bond for C-C bond formation in the presence of similar amides. Using density functional theory as a guide, we report the first site-selective C-C bond modification of a particular C-N amide bond in polyamides with a low twist angle by combining ground-state steric distortion with electronic activation.