Photoredox-Catalyzed Dimerization of Arylalkenes via an Oxidative [4+2] Cycloaddition Sequence: Synthesis of Naphthalene Derivatives

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] cycloa...

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Published in:	Advanced synthesis & catalysis Vol. 358; no. 23; pp. 3887 - 3896
Main Authors:	Wei, Donglei, Li, Yanru, Liang, Fushun
Format:	Journal Article
Language:	English
Published:	Blackwell Publishing Ltd 07-12-2016
Subjects:	[4+2] cycloaddition cascade reaction Cycloaddition Derivatives Dimerization Naphthalene naphthalene derivatives Organic chemistry Photocatalysis radical cations Radicals styrene derivatives Synthesis (chemistry) visible light photocatalysis
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Abstract	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(2H)‐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.
AbstractList	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(2H)‐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. Abstract 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. magnified image
Author	Liang, Fushun Li, Yanru Wei, Donglei
Author_xml	– sequence: 1 givenname: Donglei surname: Wei fullname: Wei, Donglei organization: Department of Chemistry, Northeast Normal University, 130024, Changchun, People's Republic of China – sequence: 2 givenname: Yanru surname: Li fullname: Li, Yanru organization: Department of Chemistry, Northeast Normal University, 130024, Changchun, People's Republic of China – sequence: 3 givenname: Fushun surname: Liang fullname: Liang, Fushun email: liangfs112@nenu.edu.cn organization: Department of Chemistry, Northeast Normal University, 130024, Changchun, People's Republic of China
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Snippet	We report a radical cation [4+2] annulation of arylalkenes to afford naphthalene derivatives using an organic photosensitizer (9‐mesityl‐10‐methylacridinium... Abstract We report a radical cation [4+2] annulation of arylalkenes to afford naphthalene derivatives using an organic photosensitizer... We report a radical cation [4+2] annulation of arylalkenes to afford naphthalene derivatives using an organic photosensitizer (9-mesityl-10-methylacridinium...
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StartPage	3887
SubjectTerms	[4+2] cycloaddition cascade reaction Cycloaddition Derivatives Dimerization Naphthalene naphthalene derivatives Organic chemistry Photocatalysis radical cations Radicals styrene derivatives Synthesis (chemistry) visible light photocatalysis
Title	Photoredox-Catalyzed Dimerization of Arylalkenes via an Oxidative [4+2] Cycloaddition Sequence: Synthesis of Naphthalene Derivatives
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