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

作者:Chan Chieh Kai; Hsueh Nai Chen; Tsai Yu Lin; Chang Meng Yang
来源:Journal of Organic Chemistry, 2017, 82(13): 7077-7084.
DOI:10.1021/acs.joc.7b01278

摘要

In this article, a facile two-step and onepot 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.

  • 出版日期2017-7-7