Bi(OTf)3-Mediated Intramolecular Olefinic Cyclization: Synthesis of Substituted Aryl-Dihydronaphthalenes and Indenes

Article abstract of DOI:10.1021/acs.joc.7b01278

In this article, a facile two-step and one-pot synthetic route for the preparation of substituted aryl dihydronaphthalenes starting from 2-allylbenzaldehydes via Grignard 1,2-addition and Bi(OTf)₃-catalyzed intramolecular olefinic cyclization has been developed. A five-membered ring indene skeleton is also prepared via olefin isomerization, 1,2-addition followed by cyclization. Some key structures are determined using single-crystal X-ray crystallography. A possible mechanism is presented herein.