Highly practical oxidation of benzylic alcohol in continuous-flow system with metal-free catalyst

Chengkou Liu; Zheng Fang; Zhao Yang; Qingwen Li; Shiyu Guo; Kai Zhang; Pingkai Ouyang; Kai Guo

doi:10.1016/j.tetlet.2015.07.069

Highly practical oxidation of benzylic alcohol in continuous-flow system with metal-free catalyst

Chengkou Liu, Zheng Fang, Zhao Yang, Qingwen Li, Shiyu Guo, Kai Zhang, Pingkai Ouyang, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

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

16 Scopus citations

Abstract

Oxidation of benzylic alcohol to ketone or aldehyde is one of the most challenging reactions in terms of green chemistry. We report herein that employing H₂O₂, catalytic amount of Br^- and acid in continuous-flow system to realize oxidation of benzylic alcohols with broad substrate scope and high selectivity. More importantly, no over oxidation to acid was obtained and it showed higher selectivity to 2° hydroxyl groups rather than 1°.

Original language	English
Pages (from-to)	5973-5976
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	44
DOIs	https://doi.org/10.1016/j.tetlet.2015.07.069
State	Published - 28 Oct 2015

Keywords

Benzylic alcohol
Chemoselective oxidation
Continuous-flow
Hydrogen peroxide
Sodium bromide

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10.1016/j.tetlet.2015.07.069

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title = "Highly practical oxidation of benzylic alcohol in continuous-flow system with metal-free catalyst",

abstract = "Oxidation of benzylic alcohol to ketone or aldehyde is one of the most challenging reactions in terms of green chemistry. We report herein that employing H2O2, catalytic amount of Br- and acid in continuous-flow system to realize oxidation of benzylic alcohols with broad substrate scope and high selectivity. More importantly, no over oxidation to acid was obtained and it showed higher selectivity to 2° hydroxyl groups rather than 1°.",

keywords = "Benzylic alcohol, Chemoselective oxidation, Continuous-flow, Hydrogen peroxide, Sodium bromide",

author = "Chengkou Liu and Zheng Fang and Zhao Yang and Qingwen Li and Shiyu Guo and Kai Zhang and Pingkai Ouyang and Kai Guo",

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T1 - Highly practical oxidation of benzylic alcohol in continuous-flow system with metal-free catalyst

AU - Liu, Chengkou

AU - Fang, Zheng

AU - Yang, Zhao

AU - Li, Qingwen

AU - Guo, Shiyu

AU - Zhang, Kai

AU - Ouyang, Pingkai

AU - Guo, Kai

PY - 2015/10/28

Y1 - 2015/10/28

N2 - Oxidation of benzylic alcohol to ketone or aldehyde is one of the most challenging reactions in terms of green chemistry. We report herein that employing H2O2, catalytic amount of Br- and acid in continuous-flow system to realize oxidation of benzylic alcohols with broad substrate scope and high selectivity. More importantly, no over oxidation to acid was obtained and it showed higher selectivity to 2° hydroxyl groups rather than 1°.

AB - Oxidation of benzylic alcohol to ketone or aldehyde is one of the most challenging reactions in terms of green chemistry. We report herein that employing H2O2, catalytic amount of Br- and acid in continuous-flow system to realize oxidation of benzylic alcohols with broad substrate scope and high selectivity. More importantly, no over oxidation to acid was obtained and it showed higher selectivity to 2° hydroxyl groups rather than 1°.

KW - Benzylic alcohol

KW - Chemoselective oxidation

KW - Continuous-flow

KW - Hydrogen peroxide

KW - Sodium bromide

UR - http://www.scopus.com/inward/record.url?scp=84944238925&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2015.07.069

DO - 10.1016/j.tetlet.2015.07.069

M3 - 文章

AN - SCOPUS:84944238925

SN - 0040-4039

VL - 56

SP - 5973

EP - 5976

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 44

ER -

Highly practical oxidation of benzylic alcohol in continuous-flow system with metal-free catalyst

Abstract

Keywords

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