3 years ago

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

Bi(OTf)3-Mediated Intramolecular Olefinic Cyclization: Synthesis of Substituted Aryl-Dihydronaphthalenes and Indenes
Yu-Lin Tsai, Nai-Chen Hsueh, Chieh-Kai Chan, Meng-Yang Chang
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01278

DOI: 10.1021/acs.joc.7b01278

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