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Photoredox‐Catalyzed Dimerization of Arylalkenes via an Oxidative [4+2] Cycloaddition Sequence: Synthesis of Naphthalene Derivatives
Author(s) -
Wei Donglei,
Li Yanru,
Liang Fushun
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600587
Subject(s) - chemistry , cycloaddition , intramolecular force , photochemistry , annulation , photoredox catalysis , naphthalene , photocatalysis , electrophile , alkene , photooxygenation , catalysis , singlet oxygen , photosensitizer , medicinal chemistry , organic chemistry , oxygen
We report a radical cation [4+2] annulation of arylalkenes to afford naphthalene derivatives using an organic photosensitizer (9‐mesityl‐10‐methylacridinium perchlorate) under visible light photocatalysis. In the presence of oxygen (in the air), the oxidative dimerization/intramolecular [4+2] cycloaddition of two alkene molecules provides 3,4‐dihydronaphthalen‐1(2 H )‐ones in good to high yields. Under a nitrogen atmosphere, (dihydro)naphthalenes were attained in moderate to excellent yields by using Selectfluor as the oxidant. The transformation proceeds via a tandem dimeric electrophilic addition/Friedel–Crafts cyclization/radical coupling/elimination sequence. This approach represents a mild and straightforward assembly of the naphthalene skeleton using a visible light photocatalytic cascade strategy.