6533b830fe1ef96bd1297085
RESEARCH PRODUCT
Light-Induced Alkylation of (Hetero)aromatic Nitriles in a Transition-Metal-Free C–C-Bond Metathesis
Benjamin LippHeiner DetertAlexander LippTill Opatzsubject
010405 organic chemistryChemistryRadicalOrganic ChemistryAlkylation010402 general chemistryPhotochemistryCleavage (embryo)Metathesis01 natural sciencesBiochemistryMedicinal chemistry0104 chemical sciencesTransition metalYield (chemistry)Light inducedPhysical and Theoretical ChemistryBond cleavagedescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2017-04-07 | Organic Letters |