Efficient photocatalytic oxygenation of aromatic alkene to 1,2-dioxetane with oxygen via electron transfer

Kei Ohkubo; Takashi Nanjo; Shunichi Fukuzumi

doi:10.1021/ol051696+

Efficient photocatalytic oxygenation of aromatic alkene to 1,2-dioxetane with oxygen via electron transfer

Kei Ohkubo
, Takashi Nanjo
, Shunichi Fukuzumi

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

91 Scopus citations

Abstract

(Chemical Equation Presented) Photocatalytic oxygenation of tetraphenylethylene (TPE) with oxygen occurs efficiently via electron-transfer reactions of TPE and oxygen with a photogenerated electron transfer state of 9-mesityl-10-methylacridniium ion, followed by the radical-coupling reaction between TPE radical cation and O₂^•- to produce 1,2-dioxetane selectively. The further photocatalytic cleavage of the O-O bond of dioxetane affords benzophenone as the final oxygenated product.

Original language	English
Pages (from-to)	4265-4268
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	19
DOIs	https://doi.org/10.1021/ol051696+
State	Published - 15 Sep 2005

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title = "Efficient photocatalytic oxygenation of aromatic alkene to 1,2-dioxetane with oxygen via electron transfer",

abstract = "(Chemical Equation Presented) Photocatalytic oxygenation of tetraphenylethylene (TPE) with oxygen occurs efficiently via electron-transfer reactions of TPE and oxygen with a photogenerated electron transfer state of 9-mesityl-10-methylacridniium ion, followed by the radical-coupling reaction between TPE radical cation and O2•- to produce 1,2-dioxetane selectively. The further photocatalytic cleavage of the O-O bond of dioxetane affords benzophenone as the final oxygenated product.",

author = "Kei Ohkubo and Takashi Nanjo and Shunichi Fukuzumi",

year = "2005",

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doi = "10.1021/ol051696+",

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journal = "Organic Letters",

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T1 - Efficient photocatalytic oxygenation of aromatic alkene to 1,2-dioxetane with oxygen via electron transfer

AU - Ohkubo, Kei

AU - Nanjo, Takashi

AU - Fukuzumi, Shunichi

PY - 2005/9/15

Y1 - 2005/9/15

N2 - (Chemical Equation Presented) Photocatalytic oxygenation of tetraphenylethylene (TPE) with oxygen occurs efficiently via electron-transfer reactions of TPE and oxygen with a photogenerated electron transfer state of 9-mesityl-10-methylacridniium ion, followed by the radical-coupling reaction between TPE radical cation and O2•- to produce 1,2-dioxetane selectively. The further photocatalytic cleavage of the O-O bond of dioxetane affords benzophenone as the final oxygenated product.

AB - (Chemical Equation Presented) Photocatalytic oxygenation of tetraphenylethylene (TPE) with oxygen occurs efficiently via electron-transfer reactions of TPE and oxygen with a photogenerated electron transfer state of 9-mesityl-10-methylacridniium ion, followed by the radical-coupling reaction between TPE radical cation and O2•- to produce 1,2-dioxetane selectively. The further photocatalytic cleavage of the O-O bond of dioxetane affords benzophenone as the final oxygenated product.

UR - https://www.scopus.com/pages/publications/25444484433

U2 - 10.1021/ol051696+

DO - 10.1021/ol051696+

M3 - Article

C2 - 16146403

AN - SCOPUS:25444484433

SN - 1523-7060

VL - 7

SP - 4265

EP - 4268

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Efficient photocatalytic oxygenation of aromatic alkene to 1,2-dioxetane with oxygen via electron transfer

Abstract

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