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Light-Induced Alkylation of (Hetero)aromatic Nitriles in a Transition-Metal-Free C–C-Bond Metathesis

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journal contribution
posted on 07.04.2017, 19:22 by Benjamin Lipp, Alexander Lipp, Heiner Detert, Till Opatz
A light-induced C–C-σ-bond metathesis was achieved through transition-metal-free activation of an unstrained C­(sp3)–C­(sp3)-σ-bond in 1-benzyl-1,2,3,4-tetrahydro­iso­quinolines. A photoredox-mediated single-electron oxidation of these precursor amines yield radical cations which undergo a homolytic cleavage of a C­(sp3)–C­(sp3)-σ-bond rather than the well-known α-C–H-scission. The resulting carbon-centered radicals are used in the ipso-substitution of (hetero)­aromatic nitriles proceeding through another single-electron transfer-mediated C–C-bond cleavage and formation.