Poly(ethylene glycol)-supported nitroxyls: branched catalysts for the selective oxidation of alcohols

The Journal of Organic Chemistry
Pedro FerreiraWayne Hayes

Abstract

Nitroxyl radicals such as 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) are highly selective oxidation catalysts for the conversion of primary alcohols into the corresponding aldehydes. In this study, direct tethering of TEMPO units onto linear poly(ethylene glycol) (PEG) has afforded macromolecular catalysts that exhibit solubility in both aqueous and organic solvents. Recovery of the dissolved polymer-supported catalyst has been carried out by precipitation with a suitable solvent such as diethyl ether. The high catalyst activities and selectivities associated traditionally with nitroxyl-mediated oxidations of alcohols are retained by the series of "linker-less" linear PEG-TEMPO catalysts in which the TEMPO moiety is coupled directly to the PEG support. Although the selectivity remains unaltered, upon recycling of the linker-less polymer-supported catalysts, extended reaction times are required to maintain high yields of the desired carbonyl compounds. Alternatively, attachment of two nitroxyl radicals onto each functionalized PEG chain terminus via a 5-hydroxyisophthalic acid linker affords branched polymer-supported catalysts. In stark contrast to the linker-less catalysts, these branched nitroxyls exhibit catalytic activiti...Continue Reading

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Citations

May 2, 2017·Chemical Reviews·Chengna DaiZhigang Lei
Mar 8, 2005·Organic & Biomolecular Chemistry·Tracy Yuen Sze ButPatrick H Toy
Sep 21, 2010·Chemistry : a European Journal·Alexander K Tucker-Schwartz, Robin L Garrell
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Feb 13, 2009·Chemical Reviews·David E BergbreiterChayanant Hongfa
Oct 9, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Jonghyeon LeeMin Kim

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