Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstraß 40, 48149, Münster, Germany.
Chemistry. 2019 Jan 7;25(2):516-520. doi: 10.1002/chem.201805490. Epub 2018 Dec 11.
A transition-metal-free radical 1,2-amidoalkynylation of unactivated alkenes is presented. α-Amido-oxy acids were used as amidyl radical precursors, which were oxidized by an organic photoredox catalyst (4CzlPN). The electrophilic N-radicals chemoselectively reacted with various aliphatic alkenes and the adduct radicals were then trapped by ethynylbenziodoxolone (EBX) reagents to eventually provide the amidoalkynylation products. These transformations, which were conducted under practical and mild conditions, showed high functional group tolerance and broad substrate scope. Mechanistic studies supported the radical nature of these cascades.
本文报道了一种无过渡金属自由基 1,2-酰胺基炔烃化反应。α-酰胺基-氧基酸被用作酰胺基自由基前体，它们被有机光氧化还原催化剂（4CzlPN）氧化。亲电 N-自由基选择性地与各种脂肪族烯烃反应，然后加合物自由基被乙炔基苯并碘恶唑酮（EBX）试剂捕获，最终得到酰胺基炔烃化产物。这些在实际和温和条件下进行的转化具有高官能团容忍度和广泛的底物范围。机理研究支持了这些级联反应的自由基性质。
