HNTf2-catalyzed regioselective preparation of polysubstituted naphthalene derivatives through alkyne-aldehyde coupling.
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.
PSL Research University, Chimie ParisTech - CNRS, Institut de Recherche de Chimie Paris, 75005, Paris, France.
Sudipta
S
Ponra
PSL Research University, Chimie ParisTech - CNRS, Institut de Recherche de Chimie Paris, 75005, Paris, France.
Maxime R
MR
Vitale
PSL Research University, Chimie ParisTech - CNRS, Institut de Recherche de Chimie Paris, 75005, Paris, France.
Véronique
V
Michelet
PSL Research University, Chimie ParisTech - CNRS, Institut de Recherche de Chimie Paris, 75005, Paris, France.
Virginie
V
Ratovelomanana-Vidal