Visible-Spectrum Solar-Light-Mediated Benzylic C-H Oxygenation Using 9,10-Dibromoanthracene As an Initiator

Sourav K. Santra; Alex M. Szpilman

doi:10.1021/acs.joc.0c01720

Visible-Spectrum Solar-Light-Mediated Benzylic C-H Oxygenation Using 9,10-Dibromoanthracene As an Initiator

Sourav K. Santra, Alex M. Szpilman

Department of Chemical Sciences

Ariel University

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

Abstract

We report a visible-light-mediated benzylic C-H oxygenation reaction. The reaction is initiated by solar light or the blue LED activation of 9,10-dibromoanthracene in a reaction with oxygen and takes place at ambient temperature and air pressure. Secondary benzylic positions are oxygenated to ketones, while tertiary benzylic carbons are oxygenated to give hydroperoxides. Notably, cumene hydroperoxide is produced in a higher yield and at milder conditions than the currently employed industrial conditions.

Original language	English
Pages (from-to)	1164-1171
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	86
Issue number	1
DOIs	https://doi.org/10.1021/acs.joc.0c01720
State	Published - 1 Jan 2021

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/acs.joc.0c01720

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abstract = "We report a visible-light-mediated benzylic C-H oxygenation reaction. The reaction is initiated by solar light or the blue LED activation of 9,10-dibromoanthracene in a reaction with oxygen and takes place at ambient temperature and air pressure. Secondary benzylic positions are oxygenated to ketones, while tertiary benzylic carbons are oxygenated to give hydroperoxides. Notably, cumene hydroperoxide is produced in a higher yield and at milder conditions than the currently employed industrial conditions.",

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Y1 - 2021/1/1

N2 - We report a visible-light-mediated benzylic C-H oxygenation reaction. The reaction is initiated by solar light or the blue LED activation of 9,10-dibromoanthracene in a reaction with oxygen and takes place at ambient temperature and air pressure. Secondary benzylic positions are oxygenated to ketones, while tertiary benzylic carbons are oxygenated to give hydroperoxides. Notably, cumene hydroperoxide is produced in a higher yield and at milder conditions than the currently employed industrial conditions.

AB - We report a visible-light-mediated benzylic C-H oxygenation reaction. The reaction is initiated by solar light or the blue LED activation of 9,10-dibromoanthracene in a reaction with oxygen and takes place at ambient temperature and air pressure. Secondary benzylic positions are oxygenated to ketones, while tertiary benzylic carbons are oxygenated to give hydroperoxides. Notably, cumene hydroperoxide is produced in a higher yield and at milder conditions than the currently employed industrial conditions.

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U2 - 10.1021/acs.joc.0c01720

DO - 10.1021/acs.joc.0c01720

M3 - مقالة

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JF - Journal of Organic Chemistry

IS - 1

ER -

Visible-Spectrum Solar-Light-Mediated Benzylic C-H Oxygenation Using 9,10-Dibromoanthracene As an Initiator

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