Reactions of Cyclohexenyliodonium Salts

Okuyama, Tadashi; Fujita, Morifumi

doi:10.1007/s11178-005-0330-8

Cited by 10 publications

(9 citation statements)

References 30 publications

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“…The preparation, structural features, and reactivity of alkenyliodonium salts have been previously summarized in the reviews of Ochiai, , Okuyama, ,, and Zefirov . This section will discuss recent developments in the synthesis and applications of alkenyl(aryl)iodonium salts.…”

Section: Synthetic Applications Of Trivalent Iodine Compoundsmentioning

confidence: 99%

“…The chemistry of polyvalent iodine compounds has been previously summarized in four books, ,− several book chapters, ,− and numerous comprehensive reviews. − Many specialized reviews on synthetic applications of specific classes of polyvalent iodine compounds have been published. − …”

Section: Introductionmentioning

confidence: 99%

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Advances in Synthetic Applications of Hypervalent Iodine Compounds

2016

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The preparation, structure, and chemistry of hypervalent iodine compounds are reviewed with emphasis on their synthetic application. Compounds of iodine possess reactivity similar to that of transition metals, but have the advantage of environmental sustainability and efficient utilization of natural resources. These compounds are widely used in organic synthesis as selective oxidants and environmentally friendly reagents. Synthetic uses of hypervalent iodine reagents in halogenation reactions, various oxidations, rearrangements, aminations, C−C bond-forming reactions, and transition metal-catalyzed reactions are summarized and discussed. Recent discovery of hypervalent catalytic systems and recyclable reagents, and the development of new enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important achievement in the field of hypervalent iodine chemistry. One of the goals of this Review is to attract the attention of the scientific community as to the benefits of using hypervalent iodine compounds as an environmentally sustainable alternative to heavy metals.

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Section: Synthetic Applications Of Trivalent Iodine Compoundsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Advances in Synthetic Applications of Hypervalent Iodine Compounds

2016

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“…Numerous reviews on specific classes of polyvalent iodine compounds and their synthetic applications have recently been published 18–61. Most notable are the specialized reviews on [hydroxy(tosyloxy)iodo]benzene,41 the chemistry and synthetic applications of iodonium salts,29,36,38,42,43,46,47,54,55 the chemistry of iodonium ylides,56–58 the chemistry of iminoiodanes,28 hypervalent iodine fluorides,27 electrophilic perfluoroalkylations,44 perfluoroorgano hypervalent iodine compounds,61 the chemistry of benziodoxoles,24,45 polymer-supported hypervalent iodine reagents,30 hypervalent iodine-mediated ring contraction reactions,21 application of hypervalent iodine in the synthesis of heterocycles,25,40 application of hypervalent iodine in the oxidation of phenolic compounds,32,34,50–53,60 oxidation of carbonyl compounds with organohypervalent iodine reagents,37 application of hypervalent iodine in (hetero)biaryl coupling reactions,31 phosphorolytic reactivity of o -iodosylcarboxylates,33 coordination of hypervalent iodine,19 transition metal catalyzed reactions of hypervalent iodine compounds,18 radical reactions of hypervalent iodine,35,39 stereoselective reactions of hypervalent iodine electrophiles,48 catalytic applications of organoiodine compounds,20,49 and synthetic applications of pentavalent iodine reagents 22,23,26,59…”

Section: Introductionmentioning

confidence: 99%

Chemistry of Polyvalent Iodine

2008

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“…Compound 11 is the decomposition product of 10 . The formation of compounds similar to 10 and 11 was shown for S N 2 pathway for vinylic nucleophilic substitution reactions in alkylvinyl(phenyl)iodonium salts …”

Section: Discussionmentioning

confidence: 62%

“…Iodonium compounds attract considerable attention due to their wide application in organic synthesis and in photoinduced initiation of cationic polymerization . A great variety of reactions occurring with participation of iodonium compounds involve radicals.…”

Section: Introductionmentioning

confidence: 99%

Dichloromethane as solvent and reagent: a case study of photoinduced reactions in mixed phosphonium‐iodonium ylide

Левина

Klimovich

Vinogradov

et al. 2018

J of Physical Organic Chem

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Several years ago the photoinduced reaction of mixed phosphonium-iodonium ylides (1) with acetylenes (2) to give λ 5 -phosphinolines (3) and substituted furans (4) was described. This reaction is one-pot, metal-free synthesis of heterocycles 3 and 4 with the yields of 40% to 80%. The reaction proceeds only in dichloromethane (DCM) at the high ylide concentrations (>0.01 mol/L). The product analysis by 31 P NMR, electrospray ionization mass spectrometry, UVvis spectrophotometry, and the dynamic light scattering study of the self-aggregation of the ylide in DCM showed a dual role of the solvent in the photoinduced reactions of mixed phosphonium-iodonium ylide: (i) at the low ylide concentrations (<0.01 mol/L), the conjugated photoinitiation of the chain reaction in DCM results in the formation of chlorine-containing products and (ii) at the high ylide concentrations (>0.01 mol/L), the photolysis mechanism is determined by self-organization of the ylide molecules to give large stable aggregates in DCM, in which the target heterocycles are synthesized. Two important issues follow from the study. First, the annulation reaction between mixed phosphonium-iodonium ylide and acetylenes occurs only when the reactive intermediates are in close proximity to one other, and, second, DCM is not inert reagent in reactions occurring with participation of radicals and in one form or another can participate in photoinduced radical reactions of various solutes.KEYWORDS annulation with acetylenes, dichloromethane, phosphonium-iodonium ylides, radical reactions, selfassembly This article is dedicated with respect and affection to the memory of the late Prof. Nikolay S. Zefirov.

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Reactions of Cyclohexenyliodonium Salts

Cited by 10 publications

References 30 publications

Advances in Synthetic Applications of Hypervalent Iodine Compounds

Advances in Synthetic Applications of Hypervalent Iodine Compounds

Chemistry of Polyvalent Iodine

Dichloromethane as solvent and reagent: a case study of photoinduced reactions in mixed phosphonium‐iodonium ylide

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