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

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

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...

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Bibliographic Details
Published in:Organic letters Vol. 19; no. 8; pp. 2054 - 2057
Main Authors: Lipp, Benjamin, Lipp, Alexander, Detert, Heiner, Opatz, Till
Format: Journal Article
Language:English
Published: United States American Chemical Society 21-04-2017
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b00652