Polymer-Supported Hypervalent Iodine Reagents

Togo, Hideo; Sakuratani, Kenji

doi:10.1055/s-2002-35575

Cited by 104 publications

(47 citation statements)

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“…[30] In the presence of 1 mol % of 4-hydroxy-TEMPO immobilized on insoluble but readily swellable JandaJel [31] (loading 2.0 mmol g À1 ), and of polystyrene bound (diacetoxy)-iodosobenzene (2 mol equivs. ), [32] aldehydes and ketones were obtained from the corresponding alcohols in fair to quantitative yields after 5-48 h in dichloroethane at 70 8C. The very high yield observed in the oxidation of 2-phenylethanol (96 %) was maintained for two subsequent reaction cycles in which the catalyst was recycled and the oxidant was replenished [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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“…One such reaction is the oxidative rearrangement of cycloalkenes and cycloalkanones, which leads to a ring contraction. Although several reviews concerning hypervalent iodine chemistry have been published [4][5][6][7][8][9][10][11][12][13][14][15], none of them covered ring contraction reactions in a comprehensive manner. This review intends to cover the literature related to the ring contraction reaction of cyclic ketones and olefins promoted by hypervalent iodine.…”

Section: Introductionmentioning

confidence: 99%

Hypervalent Iodine–Mediated Ring Contraction Reactions

Silva

2006

Molecules

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Hypervalent iodine reagents constitute a powerful tool in modern synthetic organic chemistry, promoting several important reactions. One such reaction is the ring contraction of cycloalkenes and cycloalkanones promoted by iodine(III) compounds, such as iodobenzene diacetate, iodosylbenzene, iodotoluene difluoride, and [hydroxy(tosyloxy)-iodo]benzene (Koser´s reagent). This review covers all the literature related to the ring contraction of cyclic ketones and olefins promoted by iodine(III) species.

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“…Interestingly, 1b showed sufficiently high reactivities to give the cyanated products in a yield comparable to or better than PIFA. In contrast, the conventional polymersupported reagents, 18,19) poly(diacetoxyiodo)styrene (PDAIS) and poly[bis(trifluoroacetoxy)iodo]styrene (PBTIS), also provided the cyanated products, but the yields were considerably lower than those of 1b due to the insolubility of PDAIS and PBTIS. Thiophenes 5 have similar oxidation potentials as N-tosyl pyrroles, 20,21) and thus are applicable for the cyanating reaction ( Table 2).…”

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confidence: 99%