Aromatic Homo-Nazarov-Type Cyclization of Benzonorcaradienes: Stereoselective Synthesis of Hydrochrysenes

摘要

Formal homo-Nazarov cyclization of benzonorcaradienes produced by intramolecular hydroarylation of arylated alkynylcyclopropanes promoted by TfOH has been described, providing stereoselective access to highly substituted hydrochrysenes. An unprecedented 1,2-acyl migration occurred for the 2-heteroaroyl substrates, thus giving the same products as their 3heteroaroyl analogs. Moreover, these products could be readily oxidized by air to fully pi-conjugated chrysenes after decarboxylation.

关键词