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σ N–C Bond Difunctionalization in Bridged Twisted Amides: Sew-and-Cut Activation Approach to Functionalized Isoquinolines

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journal contribution
posted on 2017-04-24, 16:03 authored by Feng Hu, Pradeep Nareddy, Roger Lalancette, Frank Jordan, Michal Szostak
A rare example of highly selective σ N–C bond difunctionalization in bridged twisted lactams through N–C cleavage has been achieved. In combination with the intramolecular Heck cyclization, this method affords a two-step bond reorganization event (“sew-and-cut”) to access functionalized isoquinoline ring systems directly with high atom economy. C–H bond functionalizations directed by a weakly coordinating bridged amide bond increase scaffold diversity. Preliminary mechanistic studies on the effect of amide distortion and the role of electrophile in this unusual σ N–C amide difunctionalization are described.

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