HNTf2-catalyzed regioselective preparation of polysubstituted naphthalene derivatives through alkyne-aldehyde coupling

The Journal of Organic Chemistry
Sudipta PonraVirginie Ratovelomanana-Vidal

Abstract

We report herein the preparation of polysubstituted naphthalene derivatives by the original Brønsted-acid-catalyzed benzannulation reaction of phenylacetaldehydes with alkynes. This reaction, which was usually performed with Lewis acids under thermal activation, is efficiently promoted by 15 mol % of triflimide (HNTf2) at room temperature under metal-free and mild reaction conditions and leads with a perfect regioselectivity to a wide variety of diversely functionalized naphthalenes in 41-78% yield. A catalytic cycle is proposed together with some further applications of this catalytic system in the related benzannulation transformations of epoxide and acetal derivatives.

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Citations

Jul 29, 2015·Angewandte Chemie·Fateme S EmamiBartosz A Grzybowski
Sep 26, 2020·Chemistry : a European Journal·Patrick Yves ToullecJean-Marc Sotiropoulos
Sep 27, 2018·Chemical Reviews·Wanxiang Zhao, Jianwei Sun

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