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A new Ag-catalyzed oxidative bicyclization of N-tethered 1,7-enynes with alkylcarboxylic acids for forming 41 examples of polycyclic 3,4-dihydroquinolin-2(1H)-ones has been established using readily accessible K2S2O8 as an oxidant. The reaction pathway involves a silver-catalyzed decarboxylation/in situ-generated C-center radical-triggered α,β-conjugated addition/6-exo-dig cyclization/H-abstraction/5-endo-trig cyclization/SET sequence, allowing direct site-selective decarboxylative C(sp3)–H functionalization toward the formation of multiple C–C bonds and rapid construction of complex spiroheterocycles.

rsc advances

Oxidative bicyclization ofN-tethered 1,7-enynes toward polycyclic 3,4-dihydroquinolin-2(1H)-onesviasite-selective decarboxylative C(sp3)–H functionalization