Organocatalytic Aerobic Oxidation of Benzylic sp3 C-H Bonds of Ethers and Alkylarenes Promoted by a Recyclable TEMPO Catalyst

Zhiguang Zhang; Yuan Gao; Yuan Liu; Jianjun Li; Hexin Xie; Hao Li; Wei Wang

doi:10.1021/acs.orglett.5b02877

Organocatalytic Aerobic Oxidation of Benzylic sp³ C-H Bonds of Ethers and Alkylarenes Promoted by a Recyclable TEMPO Catalyst

Zhiguang Zhang, Yuan Gao, Yuan Liu, Jianjun Li, Hexin Xie, Hao Li, Wei Wang

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

84 Scopus citations

Abstract

An entirely metal-free catalyst system consisting of an easily prepared recyclable new TEMPO derived sulfonic salt catalyst, and mineral acids (NaNO₂ and HCl) has been developed for selective aerobic oxidation of structurally diverse benzylic sp³ C-H bonds of ethers and alkylarenes. The mild reaction conditions allow for the generation of synthetically and biologically valued isochromanones and xanthones from readily accessible alkyl aromatic precursors in good yields.

Original language	English (US)
Pages (from-to)	5492-5495
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.5b02877
State	Published - Nov 6 2015
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "An entirely metal-free catalyst system consisting of an easily prepared recyclable new TEMPO derived sulfonic salt catalyst, and mineral acids (NaNO2 and HCl) has been developed for selective aerobic oxidation of structurally diverse benzylic sp3 C-H bonds of ethers and alkylarenes. The mild reaction conditions allow for the generation of synthetically and biologically valued isochromanones and xanthones from readily accessible alkyl aromatic precursors in good yields.",

author = "Zhiguang Zhang and Yuan Gao and Yuan Liu and Jianjun Li and Hexin Xie and Hao Li and Wei Wang",

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T1 - Organocatalytic Aerobic Oxidation of Benzylic sp3 C-H Bonds of Ethers and Alkylarenes Promoted by a Recyclable TEMPO Catalyst

AU - Zhang, Zhiguang

AU - Gao, Yuan

AU - Liu, Yuan

AU - Li, Jianjun

AU - Xie, Hexin

AU - Li, Hao

AU - Wang, Wei

PY - 2015/11/6

Y1 - 2015/11/6

N2 - An entirely metal-free catalyst system consisting of an easily prepared recyclable new TEMPO derived sulfonic salt catalyst, and mineral acids (NaNO2 and HCl) has been developed for selective aerobic oxidation of structurally diverse benzylic sp3 C-H bonds of ethers and alkylarenes. The mild reaction conditions allow for the generation of synthetically and biologically valued isochromanones and xanthones from readily accessible alkyl aromatic precursors in good yields.

AB - An entirely metal-free catalyst system consisting of an easily prepared recyclable new TEMPO derived sulfonic salt catalyst, and mineral acids (NaNO2 and HCl) has been developed for selective aerobic oxidation of structurally diverse benzylic sp3 C-H bonds of ethers and alkylarenes. The mild reaction conditions allow for the generation of synthetically and biologically valued isochromanones and xanthones from readily accessible alkyl aromatic precursors in good yields.

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U2 - 10.1021/acs.orglett.5b02877

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JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Organocatalytic Aerobic Oxidation of Benzylic sp³ C-H Bonds of Ethers and Alkylarenes Promoted by a Recyclable TEMPO Catalyst

Abstract

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