Anhydrides of Real and Hypothetical [Hydroxy(R−O)iodo]benzenes

Richter, Helen W.; Paul, Noel M.; Ray, Dale G.; Ray, Charlotte A.; Liable‐Sands, Louise M.; Concolino, Tom; Lam, Matthew; Rheingold, Arnold L.; Koser, Gerald F.; Golen, James A.

doi:10.1021/ic1007318

Cited by 6 publications

(4 citation statements)

References 37 publications

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“…On the basis of the reported X-ray structures of several [hydroxy(sulfonyloxy)iodo]arenes, it can be stated that the introduction of a substituent in phenyl ring of HTIB 312 does not have any significant effect on the geometry at the hypervalent iodine center. X-ray crystal structures of HTIB derivatives, [hydroxy(mesyloxy)iodo]benzene, and the respective oxo-bridged anhydride compounds have been reported by Richter and co-workers . The molecular geometry of [hydroxy(mesyloxy)iodo]benzene is very similar to that of HTIB 312 .…”

Section: Synthetic Applications Of Trivalent Iodine Compoundsmentioning

confidence: 99%

“…X-ray crystal structures of HTIB derivatives, [hydroxy-(mesyloxy)iodo]benzene, and the respective oxo-bridged anhydride compounds have been reported by Richter and coworkers. 743 The molecular geometry of [hydroxy(mesyloxy)iodo]benzene is very similar to that of HTIB 312. [Hydroxy-(mesyloxy)iodo]benzene and the respective oxo-bridged mesylate form dimers in the solid state due to intramolecular I•••O secondary bonding.…”

Section: [Bis(acyloxy)iodo]arenesmentioning

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: [Bis(acyloxy)iodo]arenesmentioning

confidence: 99%

Advances in Synthetic Applications of Hypervalent Iodine Compounds

2016

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“…An equally extensive study of the anhydrides of [hydroxy(L-O)]iodobenzene (L = methanesulfanato, toluenesulfanato, chloroaceto or iodoaceto) has been performed. 82 This study in combination with exhaustive literature data allowed a comprehensive picture of bonding interactions with the iodonium centre to be formulated. Coordination numbers used by iodine range from 5-9 and the electron domain geometries (EDG) cover almost the complete gamut of possible molecular geometries.…”

Section: Hypervalent Halogen Compoundsmentioning

confidence: 99%

“…An equally extensive study of the anhydrides of [hydroxy(L-O)]iodobenzene (L = methanesulfanato, toluenesulfanato, chloroaceto or iodoaceto) has been performed. 82 X-ray crystal structures of the m-oxobis(L-O(phenyl)iodine(III)] were obtained and the electrondomain geometries explored by way of study of the secondary bonding interactions.…”

Section: Hypervalent Halogen Compoundsmentioning

confidence: 99%

Halogens

Justik

2011

Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem.

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This chapter reports on the literature published during 2010 concerning the elemental halogens and compounds containing these elements in their positive oxidation states. Its intent is to highlight discovery and provide insight into current research trends. HighlightsHighlights of the 2010 literature concerning the halogens include the preparation of the first examples of dialkyl chloronium ions, 15 a new class of electrophilic halogen sources 18 and continued vibrancy in hypervalent bromine chemistry. [56][57][58][59][60] Elemental halogens Fully 30% of the top pharmaceuticals in sale contain a fluorine atom as highlighted by a recent review. 1 Furthermore, the innate nuclear properties of 18 F as a radiotracer for positron emission tomography (PET) and 19 F as an active nucleus for magnetic resonance imaging (MRI) fosters development of methodology for the selective fluorination of biomolecules. One recent review outlines the synthesis of fluorinated nucleosides toward their use as probes for the study of biomolecular pathways. 2 It has been noted that there is an apparent monotony of structural motifs by which fluorine is incorporated into biomolecules. To address this, a greater understanding of ''emergent'' fluorinated groups such as a-fluorinated ethers, thioethers, amines and phosphines has been suggested. 3 Furthermore, the stereoselective introduction of fluorine atoms can be exploited as a conformational tool for the synthesis of shape-controlled biomolecules. 4 The use of N-F electrophilic fluorination reagents such as Selectfluor s (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis-(tetrafluoroborate)) and NFSI (N-fluorobenzenesulfonimide) continues to receive the majority of focus in organic synthesis. A versatile one-pot method for converting aromatic and heteroaromatic halides by halide-Mg exchange and electrophilic fluorination of organomagnesium reagents with NFSI has now been developed which can even be applied to sterically congested substrates. 5 A potentially new role for fluorine in

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Structural Chemistry of Hypervalent Iodine Compounds

Justik

2018

Patai's Chemistry of Functional Groups

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To quote the modernist architectural mantra: “form follows function.” HVI compounds possess highly unique geometric features, which are highly tunable toward reactivity, making them impressively useful tools in modern synthetic chemistry. This chapter will endeavor to discuss the latest investigations into the structures of λ 3 ‐ and λ 5 ‐iodanes and revisit the past work with fresh insight. A new taxonomy for organizing hypervalent iodine compounds by structure will be introduced. The latest understanding of halogen bonding will be applied to the long‐observed “secondary‐bonding” interactions present in many solid‐state structures. These interactions are now understood to play a key role in the opening stages of reaction mechanisms involving hypervalent iodine reagents, especially in arylation chemistry. The X‐ray crystallographic data from a representative scope of iodanes will be complied in one work, as an easily accessible reference for those new to the field or those cogitating new possible structural motifs to solve synthetic challenges.

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Anhydrides of Real and Hypothetical [Hydroxy(R−O)iodo]benzenes

Cited by 6 publications

References 37 publications

Advances in Synthetic Applications of Hypervalent Iodine Compounds

Advances in Synthetic Applications of Hypervalent Iodine Compounds

Halogens

Structural Chemistry of Hypervalent Iodine Compounds

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