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Copper catalyzed oxidation of benzylic alcohols in water with H2O2

Paper ID Volume ID Publish Year Pages File Format Full-Text
41284 45883 2012 8 PDF Available
Title
Copper catalyzed oxidation of benzylic alcohols in water with H2O2
Abstract

A straightforward, efficient and sustainable copper catalyzed method was developed for oxidation of benzylic alcohols with 30% H2O2 in water. The reaction proceeded with CuSO4 catalyst (1 mol%) at 100 °C without additional base or ligand. Primary benzylic alcohols were converted almost quantitatively to aldehydes with 70–90% selectivity, corresponding acids being the major side products. Also secondary benzylic alcohols afforded the corresponding ketones in high conversion with selectivities greater than 90%. It was demonstrated that the CuSO4 catalyst can be recycled and reused at least for three runs, even though with some loss of catalytic activity. Selectivity of the CuSO4 based catalyst system could be further increased by using 2-N-(p-fluorophenyl)-pyrrolecarbaldimine (1) as a ligand in combination with TEMPO in K2CO3 solution. The catalyst system was individually optimized (1 mol% CuSO4, 2 mol% 1, 0.1 M K2CO3 and 5 mol% TEMPO) for a wide range of benzylic and allylic alcohols, which were quantitatively and selectively converted into the corresponding aldehydes with 3 eq. of H2O2 in 1 h.

Graphical abstract.Figure optionsDownload full-size imageDownload high-quality image (124 K)Download as PowerPoint slideHighlights► Efficient Cu-catalyzed methods for alcohol oxidation with H2O2 were introduced. ► CuSO4 alone oxidizes selectively secondary alcohols in sole water. ► With a ligand modified catalyst, the oxidation is selective toward primary alcohols.

Keywords
Oxidation; Alcohols; Copper; Hydrogen peroxide; Water
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Copper catalyzed oxidation of benzylic alcohols in water with H2O2
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volumes 411–412, 16 January 2012, Pages 180–187
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
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