iodine ball hypervalent

1 Introduction. The use of hypervalent iodine reagents in organic synthesis has regained much of its interest in the past decades. These reagents are non-metallic, environmentally friendly and offer a broad range of reactivities whilst, at the same time, typically being mild and highly efficient. 1 Yet, despite the popularity of hypervalent …

Scheme 2.General mechanism of activation of thiogalactoside by hypervalent iodine 2.1.1. O-glycosides PhIO mediated: O] in situ. One of the first uses of hypervalent iodine was for the activation of thioglycosides. In the early 1990s when the use of hypervalent iodine reagents started to show promise in different organic …

Hypervalent iodine reagents have recently emerged as powerful tools for the functionalization of peptides and proteins. These reactive compounds have high functional group tolerance, are stable in biocompatible media, 4 and are relatively nontoxic. Over the years, a variety of acyclic and cyclic hypervalent iodine reagents have been developed.

The use of hypervalent iodine reagents has acquired an important attention for the functionalization of carbohydrate molecules in modern organic chemistry. In this review we have put our best effort to …

Abstract. This chapter describes advances in hypervalent iodine (III)-induced rearrangements reported between 2004 and 2015, beginning with Hofmann-type rearrangements and aliphatic aryl transpositions. In both reactions the iodine (III) reagent may be off-the-shelf or catalytically generated in situ. A number of stereoselective …

Introduction. During the past several decades, the chemistry of hypervalent iodine reagents (HIRs) has gained more and more attention due to their unique …

The fast access to simple (Z)-3-iodo acrylic acid derivatives which can be easily oxidized to the corresponding hypervalent iodine(III) reagents is described. They can be used for various reactions with superior or similar reactivity …

Halogen bonding acknowledged as a noteworthy weak interaction, has gained growing recognition in the field of supramolecular chemistry. In this study, we selected structurally rigid diaryliodonium ions (I(III)) with two biaxial σ-holes as halogen-bond donors, to bind with three chiral acceptor molecules bearing cholesteryl and naphthalimides with distinct …

A gold-hypervalent iodine combination was further explored for the hetero-arylation of olefins 39 by Ball et al. (2012). They designed a three-component oxyarylation reaction by using a gold catalyst and 1-hydroxy-1,2-benziodoxol-3(1 H )-one (IBA) 8 as an efficient oxidant ( Figure 5 ).

Complete the exercises below to see examples of molecules containing hypervalent atoms. Exercise (PageIndex{1}) Draw the Lewis structures for sulfur hexafluoride ((ce{SF6})). Answer. Each fluorine atom has one valence electron and will make one bond each. The sulfur has six valence electrons, and must make six bonds to form a molecule ...

on hypervalent iodine controlled chemoselectivity in the cyclization of o- alkenylbenzamides, and the work described here highlights a one-pot transformation involving an exclusive cascade sequence of

Hypervalent Iodine. Iodine was discovered in 1811 by French chemist Bernard Courtois and it was named by J. L. Gay Lussac in 1813. Its name derives from the Greek word iodes, meaning "violet-colored," reflecting both the characteristic lustrous, deep purple color of resublimed crystalline iodine as well as the colour of its vapour.

The current results show that CsI3 with space group of Pm-3n is thermodynamically stable under high pressure. Hypervalence phenomenon of iodine atoms in Pm-3n CsI3 with endless linear chain type ...

Hypervalent iodine reagents can be used as efficient oxidants in various oxidative cyclizations, fragmentations, rearrangements, and functionalizations of organic …

In most cases, the explosion is inevitable when hypervalent iodine in direct contacts with primary amines, which further restricts the solid-state synthesis. Inspired by the principle of "rule of six", it is feasible to construct azo-based polymers by hypervalent iodine oxidant in ball milling process.

Hypervalent Iodine. Iodine was discovered in 1811 by French chemist Bernard Courtois and it was named by J. L. Gay Lussac in 1813. Its name derives from the Greek word iodes, meaning "violet-colored," reflecting both the characteristic lustrous, deep purple color of resublimed crystalline iodine as well as the colour of its vapour.

Also, X-ray structural data of iodine(III) compounds with a coordination of 2 (as in iodonium salts) have never been observed. 92.6 o 87.2 o 3.06A b o n d i n g n o n a n t i 2orthgnal 3c-4e bonds o Classes of Hypervalent Iodine n Traditional classification is based on the # of carbon ligands on central iodine. For Iodinanes

Hypervalent iodine compounds are valuable and versatile reagents in synthetic organic chemistry, generating a diverse array of useful organic molecules. Owing to their non-toxic and environmentally friendly features, these reagents find potential applications in various oxidative functionalization reactions. In recent years, the use of hypervalent iodine …

Hypervalent iodine(III) reagents represent powerful metal-free alternatives in oxidation reactions [].In recent years the potential of these reagents to promote conceptually new C–N bond formations has been broadened to a significant extent [1, 2].This chapter summarizes recent advances in the field of such hypervalent iodine mediated or …

2.1 Synthesis of Quinones. The simplest dearomatizing transformation of phenols is their conversion into ortho- or para-quinones by oxygenation and/or dehydrogenation reactions.Hypervalent iodine(III) and iodine(V) reagents (i.e., λ 3 - and λ 5-iodanes) have often been used to mediate these reactions, and related reports …

Also, X-ray structural data of iodine(III) compounds with a coordination of 2 (as in iodonium salts) have never been observed. 92.6 o 87.2 o 3.06A b o n d i n g n o n …

Hypervalent iodine (III) compounds show valuable ionic reactivity due to their high electrophilicity but also express radical reactivity as single electron oxidants for carbon and heteroatom radical generation.

Different methods have been devised over past decades and synthetic molecular catalysts based on transition-metal complexes 1 or small organic compounds 2 represent the most advanced concepts in the field. 3 Within the context of small organic catalysts, chiral hypervalent iodine reagents have enabled the development of …

The addition of a hypervalent iodine compound enables the fluorination to proceed under mild conditions (25–60 °C). Abstract. An unprecedented hypervalent iodine(III) catalyzed Balz–Schiemann reaction is described. In the presence of a hypervalent iodine compound, the fluorination reaction proceeds under mild conditions …

aspects of hypervalent iodine chemistry have been published since the year of 2000, and hundreds (if not thousands) of research works utilizing hypervalent iodine reagents are …

Hypervalent iodine reagents are of considerable relevance in organic chemistry as they can provide a complementary reaction strategy to the use of traditional transition metal chemistry. Over the past two decades, there have been an increasing number of applications including stoichiometric oxidation and catalytic asymmetric …

Hypervalent iodine reagents have been extensively employed in various types of oxidative organic reactions including oxidative coupling/cyclization, bifunctionalization of olefins and cyclopropane, C–H functionalization, and oxidative rearrangement reactions. In this review, the developments of the exclusive Chemical …

The proposed use of the term halogen bond for some of the long bonds around iodine atoms in hypervalent iodine derivatives implies a conceptual frame for the bonding pattern around iodine that complements other models available in the literature for this pattern (e.g., the three-center, four-electron (3c-4e) bonding model for λ 3 -iodanes).

Asymmetric organocatalytic oxidations have been witnessed to an impressive development in the last years thanks to the establishment of important chiral hypervalent iodines(III/V). Many different approaches involving both stoichiometric and catalytic versions have provided a fundamental advance in this area within asymmetric …

Hypervalent iodine reagents have been applied in seminal reports by Gaunt using diaryliodonium salts in C–H arylation, however experimental evidence supporting a Cu(I)/Cu(III) pathway is still lacking. Therefore, while the potential of hypervalent iodine reagents in high-valent copper catalysis is immense, the continued …

1. Introduction. Hypervalent iodine reagents are environment friendly tools for the construction of simple and complex organic molecules [1,2,3,4,5,6,7,8].These reagents are potential oxidants due to their excellent oxidizing and electrophilic properties [9,10,11,12,13].The unique characteristics attributed to these reagents are non-toxicity, …

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Hypervalent iodine compounds constitute a well-established and broadly used reagent family in organic synthesis. As they are usually either used in stoichiometric quantities or generated in situ from an aryl iodide precursor using a terminal oxidant, the associated waste and separation problems pose major challenges en route to …

Hypervalent iodine compounds have emerged as versatile oxidants, with a wide range of reactivity under mild conditions, and at the same time are non-toxic, environmentally friendly, inexpensive, and easy-to-handle reagents in organic synthesis. In recent years, the use of hypervalent iodine reagents in palladium-catalyzed …

For example, hypervalent iodine reagents are a broadly useful class of selective two-electron chemical oxidants based on 3-centered, 4-electron (3c–4e) iodine–ligand bonds 11,12,13. These ...

The discovery and development of ethynyl hypervalent iodine reagents have allowed to greatly expand the transfer of alkynes as electrophilic synthons. In this feature article the progress in the field since 2018 will be presented. ... -catalyzed C2-alkynylation of indoles using pyrimidine as a directing group. 102 Using ball milling, Bolm and ...

Abstract. The preparation, structure, and chemistry of hypervalent iodine compounds are reviewed with emphasis on their …

Understanding the role of boranes in hypervalent iodine chemistry will open up new reactivities which can be utilised in organic synthesis. Due to similar …