Beilstein J. Org. Chem.2016,12, 301–308, doi:10.3762/bjoc.12.32
)-diones in good yield.
Keywords: C(sp3)–H bond functionalization; cyclization; dihydroisoquinolin-1(2H)-one; N-allylbenzamides; oxidation; Introduction
The direct and selective functionalization of an unactivated sp3 C–H bond, which belongs to an effective strategic approach in green and sustainable
alkanes resulting in alkyl-substituted oxindoles (Scheme 1a) [43]. However, cyclization of N-allylbenzamides initiated by the functionalization of sp3 C–H bonds of simple alkanes remains unexplored. Very recently, our group developed a metal-free hydroxyalkylation-initiated radical six-membered
substrate, the cyclization reaction proceeded smoothly (Scheme 1c). Herein, we report a metal-free cascade 1,2-alkyarylation of substituted N-allylbenzamides with alkanes affording 4-alkyl-substituted dihydroisoquinoline-1(2H)-ones as the product.
Results and Discussion
Initially, we selected N-methyl-N-(2
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Graphical Abstract
Scheme 1:
Cascade 1,2-difunctionalization and cyclization to construct heterocycles.