Manganese-Catalyzed Selective Oxidation of Aliphatic C-H groups and Secondary Alcohols to Ketones with Hydrogen Peroxide

Jia Jia Dong; Duenpen Unjaroen; Francesco Mecozzi; Emma C. Harvey; Pattama Saisaha; Dirk Pijper; Johannes W. de Boer; Paul Alsters; Ben L. Feringa; Wesley R. Browne

doi:10.1002/cssc.201300378

Manganese-Catalyzed Selective Oxidation of Aliphatic C-H groups and Secondary Alcohols to Ketones with Hydrogen Peroxide

Jia Jia Dong, Duenpen Unjaroen, Francesco Mecozzi, Emma C. Harvey, Pattama Saisaha, Dirk Pijper, Johannes W. de Boer, Paul Alsters, Ben L. Feringa, Wesley R. Browne^*

^*Corresponding author for this work

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Abstract

An efficient and simple method for selective oxidation of secondary alcohols and oxidation of alkanes to ketones is reported. An insitu prepared catalyst is employed based on manganese(II) salts, pyridine-2-carboxylic acid, and butanedione, which provides good-to-excellent conversions and yields with high turnover numbers (up to 10000) with H₂O₂ as oxidant at ambient temperatures. In substrates bearing multiple alcohol groups, secondary alcohols are converted to ketones selectively and, in general, benzyl CH oxidation proceeds in preference to aliphatic CH oxidation.

Original language	English
Pages (from-to)	1774-1778
Number of pages	5
Journal	Chemsuschem
Volume	6
Issue number	9
DOIs	https://doi.org/10.1002/cssc.201300378
Publication status	Published - 14-Sept-2013

Keywords

alcohol oxidation
alkane oxidation
catalysis
manganese
AEROBIC OXIDATION
METAL CATALYSIS
ACETIC-ACID
COMPLEX
MOLYBDENUM
ALKANES
EFFICIENT
METHYLTRIOXORHENIUM
HYDROXYLATION
SYSTEM

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@article{cd497fd534294e449ce36b0b445a5615,

title = "Manganese-Catalyzed Selective Oxidation of Aliphatic C-H groups and Secondary Alcohols to Ketones with Hydrogen Peroxide",

abstract = "An efficient and simple method for selective oxidation of secondary alcohols and oxidation of alkanes to ketones is reported. An insitu prepared catalyst is employed based on manganese(II) salts, pyridine-2-carboxylic acid, and butanedione, which provides good-to-excellent conversions and yields with high turnover numbers (up to 10000) with H2O2 as oxidant at ambient temperatures. In substrates bearing multiple alcohol groups, secondary alcohols are converted to ketones selectively and, in general, benzyl CH oxidation proceeds in preference to aliphatic CH oxidation.",

keywords = "alcohol oxidation, alkane oxidation, catalysis, manganese, AEROBIC OXIDATION, METAL CATALYSIS, ACETIC-ACID, COMPLEX, MOLYBDENUM, ALKANES, EFFICIENT, METHYLTRIOXORHENIUM, HYDROXYLATION, SYSTEM",

author = "Dong, {Jia Jia} and Duenpen Unjaroen and Francesco Mecozzi and Harvey, {Emma C.} and Pattama Saisaha and Dirk Pijper and {de Boer}, {Johannes W.} and Paul Alsters and Feringa, {Ben L.} and Browne, {Wesley R.}",

year = "2013",

month = sep,

day = "14",

doi = "10.1002/cssc.201300378",

language = "English",

volume = "6",

pages = "1774--1778",

journal = "Chemsuschem",

issn = "1864-5631",

publisher = "WILEY-V C H VERLAG GMBH",

number = "9",

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TY - JOUR

T1 - Manganese-Catalyzed Selective Oxidation of Aliphatic C-H groups and Secondary Alcohols to Ketones with Hydrogen Peroxide

AU - Dong, Jia Jia

AU - Unjaroen, Duenpen

AU - Mecozzi, Francesco

AU - Harvey, Emma C.

AU - Saisaha, Pattama

AU - Pijper, Dirk

AU - de Boer, Johannes W.

AU - Alsters, Paul

AU - Feringa, Ben L.

AU - Browne, Wesley R.

PY - 2013/9/14

Y1 - 2013/9/14

N2 - An efficient and simple method for selective oxidation of secondary alcohols and oxidation of alkanes to ketones is reported. An insitu prepared catalyst is employed based on manganese(II) salts, pyridine-2-carboxylic acid, and butanedione, which provides good-to-excellent conversions and yields with high turnover numbers (up to 10000) with H2O2 as oxidant at ambient temperatures. In substrates bearing multiple alcohol groups, secondary alcohols are converted to ketones selectively and, in general, benzyl CH oxidation proceeds in preference to aliphatic CH oxidation.

AB - An efficient and simple method for selective oxidation of secondary alcohols and oxidation of alkanes to ketones is reported. An insitu prepared catalyst is employed based on manganese(II) salts, pyridine-2-carboxylic acid, and butanedione, which provides good-to-excellent conversions and yields with high turnover numbers (up to 10000) with H2O2 as oxidant at ambient temperatures. In substrates bearing multiple alcohol groups, secondary alcohols are converted to ketones selectively and, in general, benzyl CH oxidation proceeds in preference to aliphatic CH oxidation.

KW - alcohol oxidation

KW - alkane oxidation

KW - catalysis

KW - manganese

KW - AEROBIC OXIDATION

KW - METAL CATALYSIS

KW - ACETIC-ACID

KW - COMPLEX

KW - MOLYBDENUM

KW - ALKANES

KW - EFFICIENT

KW - METHYLTRIOXORHENIUM

KW - HYDROXYLATION

KW - SYSTEM

U2 - 10.1002/cssc.201300378

DO - 10.1002/cssc.201300378

M3 - Article

SN - 1864-5631

VL - 6

SP - 1774

EP - 1778

JO - Chemsuschem

JF - Chemsuschem

IS - 9

ER -