Radical Cation Diels–Alder Reactions by TiO2 Photocatalysis

Radical cation Diels–Alder reactions by titanium dioxide (TiO2) photocatalysis in lithium perchlorate/nitromethane solution are described. TiO2 photocatalysis promotes reactions between electron-rich dienes and dienophiles, which would otherwise be difficult to accomplish due to electronic mismatchi...

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Bibliographic Details
Published inOrganic letters Vol. 21; no. 7; pp. 2246 - 2250
Main Authors Nakayama, Kaii, Maeta, Naoya, Horiguchi, Genki, Kamiya, Hidehiro, Okada, Yohei
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.04.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXYGEN
VISIBLE-LIGHT PHOTOCATALYSIS
CYCLOADDITIONS
ALKYLATIONS
TITANIUM-DIOXIDE
DNA LESIONS
PHOTOREDOX CATALYSIS
CARBOXYLIC-ACIDS
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Summary:Radical cation Diels–Alder reactions by titanium dioxide (TiO2) photocatalysis in lithium perchlorate/nitromethane solution are described. TiO2 photocatalysis promotes reactions between electron-rich dienes and dienophiles, which would otherwise be difficult to accomplish due to electronic mismatching. The reactions are triggered by hole oxidation of the dienophile and are completed by the excited electron reduction of the radical cation intermediate at the dispersed surface in the absence of any sacrificial substrate.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b00526