Polymeric reagents. III. Synthesis of an insoluble polymeric thioanisole and its utilization for the oxidation of alcohols

Poly(N-vinylpyrrolidone)-hydrotribromide: A new gel-type resin for alcohol oxidation and alkene dibromination

“…Several polymeric reagents have been developed for use in oxidation [1][2][3][4][5], halogenation [6,7], acylation [8][9][10], or epoxidation [11]. Moreover, different polymer supports like polystyrene [12][13][14], polyvinyl pyridine [15][16][17], poly (methyl methacrylate) [18], etc. have been used for immobilizing the reagent functions.…”

Solid Phase and Combinatorial Chemistry in the Heterocyclic Field

“…Bromination of microporous resins in the presence of a Lewis acid catalyst is generally carried out in the dark, whereby the loading degree can be conveniently controlled by the amount of bromine used in the reaction [74]. Macroreticular resins can be brominated using Br 2 and FeCl 3 [39], or by using a stoichiometric amount of thallium acetate as Lewis acid catalyst (Scheme 28.15) [76,77].…”

“…Another illustrative example of multidirectional cleavage through nucleophilic substitution is the one shown in Scheme 28.27, which is based on Weinreb amides (77). Again, the introduction of a new element of diversity and release from the polymeric support are simultaneous [139].…”

Polymer-Supported Reagents. Mild and Efficient Method of Oxidation of Alcohols

“…Insoluble polymer-supported reagents are convenient from the practical viewpoint for solving many problems in organic synthesis [7][8][9]. Polymeric thioanisole was shown to be effective [13] in the Corey oxidation of alcohols [14]. For example, anion exchangers were successfully used in the C-alkylation of phenols [10], O-alkylation of carboxylate ions [11], and synthesis of alkyl and aralkyl fluorides [12].…”

“…A polymeric support provides a specific reaction medium which favors enhanced reactivity of a number of reagents and facilitates treatment of reaction mixtures: the products can readily be isolated by simple filtration. The efficiency of polymer-supported reagents was demonstrated using fairly sensitive compounds as substrates, in particular in the oxidation of some intermediate products in the synthesis of prostaglandins [13]. Polymeric thioanisole was shown to be effective [13] in the Corey oxidation of alcohols [14].…”