Tandem Synthesis of 1,3-Disubstituted Naphthalenes via TfOH-Promoted Directed-Aldol and Friedel–Crafts Reactions
作者:Hongchen Li、Lidong Shan、Lin Min、Yunxiang Weng、Xinyan Wang、Yuefei Hu
DOI:10.1021/acs.joc.1c01713
日期:2021.11.5
A TfOH-promoted tandemsynthesis of 1,3-disubstituted naphthalenes is developed via a directed-aldol reaction and a Friedel–Crafts reaction. Two new C–C bonds and one new benzene ring are created efficiently in one pot due to the discovery of a TfOH-promoted highly chemoselective directed-aldol reaction between two different ketones with α-hydrogens.
(o-ethynylphenyl)acetyl chloride with design of a new synthetic strategy by Stillecoupling using functionalized organostannanes. The method affords excellent yields of the substituted naphthalenes and accommodates a wide variety of functional groups under mild conditions. Mechanistic studies show intramolecular cyclization as a major step following C–C bond coupling.