American Chemical Society
ol5b03100_si_003.cif (21.06 kB)

Catalytic Arylsulfonyl Radical Triggered 1,7-Enyne Bicyclizations

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posted on 2015-12-18, 00:00 authored by Yi-Long Zhu, Bo Jiang, Wen-Juan Hao, Jiang-Kai Qiu, Jun Sun, De-Cai Wang, Ping Wei, Ai-Fang Wang, Guigen Li, Shu-Jiang Tu
A new metal-free bicyclization reaction of 1,7-enynes anchored by α,β-conjugates with arylsulfonyl radicals generated in situ from sulfonyl hydrazides has been established using tert-butyl hydroperoxide and tetrabutylammonium iodide. The reactions occurred through sulfonylation/6-exo-dig/6-exo-trig bicyclization/in situ desulfonylation/5-exo-trig cyclization/alkyl or alkenyl migration cascade mechanism to give benzo­[j]­phenanthridines regioselectively.