Poly(ethylene glycol)-Supported TEMPO:  An Efficient, Recoverable Metal-Free Catalyst for the Selective Oxidation of Alcohols

Pozzi, Gianluca; Cavazzini, Marco; Quici, Silvio; Benaglia, Maurizio; Dell’Anna, Gianmaria

doi:10.1021/ol036398w

Cited by 137 publications

(52 citation statements)

References 31 publications

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“…In the first of these reports, [22] the monomethyl ether of poly(ethylene glycol) of M W 5000 daltons (MeOPEG 5000 ) was connected to 4-hydroxy-substituted TEMPO by means of a spacer containing inert ether bonds to afford compound 1. This compound was used in combination with different terminal oxidants such as bisA C H T U N G T R E N N U N G (acetoxy)iodobenzene, trichloroisocyanuric acid, and sodium hypochlorite in the oxidation of 1-octanol to octanal [Scheme 1, Eq.…”

Section: Oxoammonium Ionsmentioning

confidence: 99%

Immobilization of Organic Catalysts: When, Why, and How

2006

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This review article is divided in two parts. In the first part (Sections 2 and 3) selected examples of the publications that appeared in the literature in the period 2003–2005 in the field of immobilized organic catalysis are presented. When appropriate, the results of these publications are compared to those reported earlier and already discussed in a previous review article (see ref. 4). On the basis of this survey, in Section 4 some general considerations about when and why a supported version of an organic catalyst is worth developing are proposed. In Section 4 a list of suggestions about how the process of immobilization should be carried out is also included, taking into account several factors such as the properties of the catalyst, the nature of the support, and the mode of connection of the catalyst to the support.

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Section: Oxoammonium Ionsmentioning

confidence: 99%

Immobilization of Organic Catalysts: When, Why, and How

2006

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“…[32][33][34][35][36] In the case of ATRC, an excess of metal is used to alter an unfavorable equilibrium and create a buildup of the polymer radicals, which is essential for the bimolecular coupling reaction to proceed at a suitable rate yet otherwise unfavorable in the preparation of polymeric materials. In this contribution, silane radical atom abstraction (SRAA, Scheme 2) is introduced as a metal-free alternative to generate polystyrene (PSt) of controllable molecular weights and low PDI values by coupling of polymer radicals generated from monobrominated polystyrene (PStBr) precursors.…”

mentioning

confidence: 99%

Efficient metal‐free coupling of polystyrene chains using silane radical atom abstraction

Thakur¹,

Tillman²

2007

J. Polym. Sci. A Polym. Chem.

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“…The use of heterogeneous catalysts in the liquid phase, however, offers several advantages over homogeneous ones, such as ease of recovery and recycling, atom utility and enhanced stability [11]. TEMPO anchored to poly (ethylene glycol) (PEG) has been prepared by Pozzi et al [12] and its catalytic activity in the chemoselective oxidation of alcohols with stoichiometric amounts of organic or inorganic oxidants has been investigated. The PEG-TEMPO is a new metal free catalyst and exhibits high activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization of Cellulose Grafted N-Oxide Reagent and Its Application in Oxidation of Alkyl/Aryl Halides

Kaur¹,

Dhiman²

2011

IJOC

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Oxidation of aliphatic and aromatic halides by N-oxide functionalities supported on 4-vinyl pyridine, (4-VP), grafted cellulose is reported in the present manuscript. Synthesis of graft copolymer of cellulose and poly 4-vinyl pyridine, poly(4-VP), has been carried out using ceric ions as redox initiator. Post-grafting treatment of CellO-g-poly(4-VP) with 30% H 2 O 2 in acetic acid gives Cellulose-g-poly(4-VP) N-oxide, the polymeric supported oxidizing reagent. The polymeric support, CellO-g-poly(4-VP) N-oxide, has been used for oxidation of different alkyl/aryl halide such as 1-bromo-3-methyl butane, 2-bromo propane, 1-bromo heptane and benzyl chloride. The polymeric reagent was characterized by IR and thermo-gravimetric analysis. The oxidized products were characterized by FTIR and H 1 NMR spectral methods. The reagent was reused for the oxidation of a fresh alkyl/aryl halides and it was observed that the polymeric reagent oxidizes the compounds successfully but with little lower product yield.

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Poly(ethylene glycol)-Supported TEMPO: An Efficient, Recoverable Metal-Free Catalyst for the Selective Oxidation of Alcohols

Cited by 137 publications

References 31 publications

Immobilization of Organic Catalysts: When, Why, and How

Immobilization of Organic Catalysts: When, Why, and How

Efficient metal‐free coupling of polystyrene chains using silane radical atom abstraction

Synthesis, Characterization of Cellulose Grafted N-Oxide Reagent and Its Application in Oxidation of Alkyl/Aryl Halides

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