3 years ago

Assembly of a Benzo-Fused Bridged Ketone Scaffold from 1,5,10-Enediynes through One-Pot Ruthenium-Catalyzed Cyclization/Iodine-Mediated Oxidative Ring Expansion

Assembly of a Benzo-Fused Bridged Ketone Scaffold from 1,5,10-Enediynes through One-Pot Ruthenium-Catalyzed Cyclization/Iodine-Mediated Oxidative Ring Expansion
Kei-ichiro Nishimura, Shota Mori, Yoshihiko Yamamoto, Masatoshi Shibuya
In the presence of a cationic Ru catalyst, 1,6-diynes bearing a terminal styryl moiety underwent [2+2+2] cyclization to produce dehydrobiphenylenes fused with a five-membered ring. Although the cycloadducts were unstable toward purification, their one-pot iodine-mediated ring expansion successfully afforded unprecedented bridged ketone products containing a benzo-fused bicyclo[3.2.1] framework. Building bridges: An unprecedented bridged ketone scaffold was assembled by a one-pot tandem ruthenium-catalyzed [2+2+2] cyclization/iodine-mediated oxidative ring expansion. The [2+2+2] cyclization proceeds in the presence of a cationic Ru catalyst in THF at room temperature, and subsequent ring expansion is triggered by the addition of N-iodosuccinimide and MeOH to the reaction mixture.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201700493

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