Preparation and X-ray structures of 2-[(aryl)iodonio]benzenesulfonates: novel diaryliodonium betaines

Justik, Michael W.; Protasiewicz, John D.; Updegraff, James B.

doi:10.1016/j.tetlet.2009.08.067

Cited by 24 publications

(17 citation statements)

References 29 publications

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“…Transformations other than alkynylations have still not been broadly investigated. Arylation, for example, has remained limited to a few examples of cross‐coupling reactions . EBX reagents have been used for transformations other than simple alkynylations.…”

Section: C−c Bond Formationmentioning

confidence: 99%

Cyclic Hypervalent Iodine Reagents for Atom‐Transfer Reactions: Beyond Trifluoromethylation

et al. 2016

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Hypervalent iodine compounds are privileged reagents in organic synthesis because of their exceptional reactivity. Among these compounds, cyclic derivatives stand apart because of their enhanced stability. They have been widely used as oxidants, but their potential for functional‐group transfer has only begun to be investigated recently. The use of benziodoxol(on)es for trifluoromethylation (Togni's reagents) is already widely recognized, but other transformations have also attracted strong interest recently. In this Review, the development in the area since 2011 will be presented. After a short summary of synthetic methods to prepare benziodoxol(on)e reagents, their use to construct carbon–heteroatom and carbon–carbon bonds will be presented. In particular, the introduction of alkynes by using ethynylbenziodoxol(on)e (EBX) reagents has been highly successful. Breakthroughs in the introduction of alkoxy, azido, difluoromethyl, and cyano groups will also be described.

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Section: C−c Bond Formationmentioning

confidence: 99%

Cyclic Hypervalent Iodine Reagents for Atom‐Transfer Reactions: Beyond Trifluoromethylation

et al. 2016

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“…[39] This was indeed the case and our preliminary results on the arylation of phenols under mild and racemization-free conditions were recently reported. [28,40] A number of aspects have since been investigated to make the reaction even more general. Herein we present: 1) the use of diaryliodonium salts with different anions, which allows for smooth synthesis of the required reagents independent of substituents; 2) a broad scope of both coupling partners; 3) the synthesis of very sterically hindered diaryl ethers; 4) a large-scale reaction with isolation of the iodoarene byproduct; 5) chemoselective arylation with unsymmetric salts.…”

Section: Synthesis Of Diaryl Ethers By Arylation Of Phenolsmentioning

confidence: 99%

Metal‐Free Arylation of Oxygen Nucleophiles with Diaryliodonium Salts

Jalalian

Petersen

Olofsson

2012

Chemistry A European J

154

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Phenols and carboxylic acids are efficiently arylated with diaryliodonium salts. The reaction conditions are mild, metal free, and avoid the use of halogenated solvents, additives, and excess reagents. The products are obtained in good-to-excellent yields after short reaction times. Steric hindrance is very well tolerated, both in the nucleophile and diaryliodonium salt. The scope includes ortho- and halo-substituted products, which are difficult to obtain by metal-catalyzed protocols. Many functional groups are tolerated, including carbonyl groups, heteroatoms, and alkenes. Unsymmetric salts can be chemoselectively utilized to obtain products with hitherto unreported levels of steric congestion. The arylation has been extended to sulfonic acids, which can be converted to sulfonate esters by two different approaches. With recent advances in efficient synthetic procedures for diaryliodonium salts the reagents are now inexpensive and readily available. The iodoarene byproduct formed from the iodonium reagent can be recovered quantitatively and used to regenerate the diaryliodonium salt, which improves the atom economy.

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“…Andere Transformationen neben der Alkinylierung sind noch nicht umfassend erforscht. Beispielsweise ist die Arylierung noch auf wenige Beispiele von Kreuzkupplungen begrenzt . EBX‐Reagentien wurden für andere Transformationen als die schlichte Alkinylierung eingesetzt.…”

Section: C‐c‐bindungsbildungunclassified

Cyclische hypervalente Iodreagentien für Atomtransferreaktionen – jenseits der Trifluormethylierung

et al. 2016

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Hypervalente Iodverbindungen nehmen als Reagentien in der organischen Synthese aufgrund ihrer außergewöhnlichen Reaktivität eine Sonderstellung ein. Unter ihnen ragen cyclische Derivate wegen ihrer erhöhten Stabilität heraus. Sie finden zwar weitreichende Anwendung als Oxidationsmittel, die Erforschung ihrer Möglichkeiten zum Transfer funktioneller Gruppen begann jedoch erst kürzlich. Während die Verwendung von Benziodoxol(on)en zur Trifluormethylierung (Togni‐Reagens) schon weitgehend anerkannt ist, erfuhren vor kurzem auch andere Transformationen große Aufmerksamkeit. Der vorliegende Aufsatz bespricht die Entwicklungen auf diesem Gebiet seit 2011. Nach einer kurzen Zusammenfassung der Methoden zur Synthese von Benziodoxol(on)reagentien wird ihre Verwendung zum Aufbau von Kohlenstoff‐Heteroatom‐ und Kohlenstoff‐Kohlenstoff‐Bindungen diskutiert. Äußerst erfolgreich war die Einführung von Alkinen mithilfe von Ethinylbenziodoxol(on)(EBX)‐Reagentien. Durchbrüche bei der Einführung von Alkoxy‐, Azido‐, Difluormethyl‐ und Cyangruppen werden ebenfalls vorgestellt.

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Preparation and X-ray structures of 2-[(aryl)iodonio]benzenesulfonates: novel diaryliodonium betaines

Cited by 24 publications

References 29 publications

Cyclic Hypervalent Iodine Reagents for Atom‐Transfer Reactions: Beyond Trifluoromethylation

Cyclic Hypervalent Iodine Reagents for Atom‐Transfer Reactions: Beyond Trifluoromethylation

Metal‐Free Arylation of Oxygen Nucleophiles with Diaryliodonium Salts

Cyclische hypervalente Iodreagentien für Atomtransferreaktionen – jenseits der Trifluormethylierung

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