[3+2]-Cycloaddition reactions of 2-phenyliodonio-1,3-dioxacyclohexanemethylide: Facile synthesis of fused dihydrofuran derivatives

Asouti, Amalia; Hadjiarapoglou, Lazaros P.

doi:10.1016/s0040-4039(98)01997-2

Cited by 50 publications

(17 citation statements)

References 32 publications

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“…10,16,28,30,51 Particularly important are methods based on the use of hypervalent iodine reagents such as (diacetoxyiodo)benzene, [76][77][78][79][80][81][82][83][84][85][86][87] [bis(trifluoroacetoxy)iodo]benzene, 79,[88][89][90][91] iodosylbenzene, [92][93][94][95] [hydroxy(tosyloxy)iodo]arenes, [96][97][98][99] recyclable iodine(III) compounds, 100 in situ generated iodine(III) species, 76,[101][102][103][104][105][106] and iodonium ylides. [107][108][109][110][111][112][113] The hypervalent-iodine(III)-mediated cyclization of Npropargylamides represents a useful synthetic methodology for the construction of the oxazole nucleus. This methodology is applicable to the synthesis of substituted oxazoles bearing nitrogen-containing groups, 76 fluoride,…”

Section: Scheme 9 Preparation Of 4-oxazoline Compounds From Iodonium mentioning

confidence: 99%

“…Iodonium ylides and various nitriles can be converted into the corresponding oxazoles in moderate to good yields. [107][108][109][110][111][112][113] For example, dimedone-derived iodonium ylide 29, reacting with nitriles in the presence of a metal catalyst, can be easily transformed into ring-fused oxazole compounds bearing a monocarbonyl group 51 (Scheme 16). 108 The key nitrilium intermediates are probably generated from iodonium salts reacting with nitrile in the presence of the rhodium catalyst, followed by cyclization to form the respective ring-fused oxazoles.…”

Section: Scheme 15 Oxidative Cycloaddition Of Dicarbonyl Compounds Wimentioning

confidence: 99%

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Synthesis of Oxazoline and Oxazole Derivatives by Hypervalent-Iodine-Mediated Oxidative Cycloaddition Reactions

et al. 2020

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Organohypervalent iodine reagents are widely used for the preparation of various oxazolines, oxazoles, isoxazolines, and isoxazoles. In the formation of these heterocyclic compounds, hypervalent iodine species can serve as the activating reagents for various substrates, as well as the heteroatom donor reagents. In recent research, both chemical and electrochemical approaches toward generation of hypervalent iodine species have been utilized. The in situ generated active species can react with appropriate substrates to give the corresponding heterocyclic products. In this short review, we summarize the hypervalent-iodine-mediated preparation of oxazolines, oxazoles, isoxazolines, and isoxazoles starting from various substrates.1 Introduction2 Synthesis of Oxazolines3 Synthesis of Oxazoles4 Synthesis of Isoxazolines5 Synthesis of Isoxazoles6 Conclusion

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Section: Scheme 9 Preparation Of 4-oxazoline Compounds From Iodonium mentioning

confidence: 99%

Section: Scheme 15 Oxidative Cycloaddition Of Dicarbonyl Compounds Wimentioning

confidence: 99%

Synthesis of Oxazoline and Oxazole Derivatives by Hypervalent-Iodine-Mediated Oxidative Cycloaddition Reactions

et al. 2020

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“…Phenyliodoniumylide kamen auch in einer Reihe von Cycloadditionen zum Einsatz, wie [3+2]‐Cycloadditionen mit Kohlenstoffdisulfid, Nitrilen 86 oder terminalen Alkinen 87 , Alkenen 88 und Carbodiimiden 89 , bei denen die Heterobicyclen 90 – 93 gebildet wurden (Schema ).…”

Section: Phenyliodonium‐ Und Sulfoniumylideunclassified

Neue Ansätze für die Synthese von Metallcarbenen

Jia

2016

Angewandte Chemie

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Metallcarbene sind vielseitige Verbindungen, deren Reaktivität sowohl durch das Metall als auch den Liganden gesteuert werden kann. Zur Synthese von Metallcarbenen nutzt man im Allgemeinen die Stickstoff‐Eliminierung von Diazoverbindungen, die allerdings häufig instabil, explosiv und toxisch sind, was ihren Einsatz in großskaligen Synthesen einschränkt. Demzufolge gibt es eine intensive Suche nach nachhaltigen und ungefährlichen Ersatzsubstraten für die zuverlässige Herstellung von Metallcarbenen. In diesem Aufsatz fassen wir die wichtigsten Fortschritte bei der Erzeugung, katalytischen Reaktionen und der Selektivitätskontrolle von Metallcarbenen zusammen, die nicht aus Diazoverbindungen gebildet wurden.

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“…61 Iodonium ylides like can react photochemically in a [2+3]-cycloaddition yielding dihydrofuran derivatives of type . 62 This photochemical reaction has previously been applied in the synthesis of annulated aromatic compounds and proceeds probably through 6-membered intermediate iodanes. 63 TpurrÃ $…”

Section: Tpurrãmentioning

confidence: 99%

Hypervalent Iodine Compounds: Recent Advances in Synthetic Applications

Wirth¹

1999

Synthesis

237

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5HFHLYHG $SULO $EVWUDFW Recent advances in reactions with hypervalent iodine(III) and iodine(V) compounds are reviewed. Particular emphasis is put on synthetic applications of hypervalent iodine reagents. Hypervalent Iodine Compounds: Recent Advances in Synthetic Applications Synthesis 1999, No. 8, 1271-1287 ISSN 0039-7881 © Thieme Stuttgart · New York I NH O X I O NH 2 + OTf -OR 109 X = OAc, OTs, OMs, N 3 , OTf ROH, H +

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[3+2]-Cycloaddition reactions of 2-phenyliodonio-1,3-dioxacyclohexanemethylide: Facile synthesis of fused dihydrofuran derivatives

Cited by 50 publications

References 32 publications

Synthesis of Oxazoline and Oxazole Derivatives by Hypervalent-Iodine-Mediated Oxidative Cycloaddition Reactions

Synthesis of Oxazoline and Oxazole Derivatives by Hypervalent-Iodine-Mediated Oxidative Cycloaddition Reactions

Neue Ansätze für die Synthese von Metallcarbenen

Hypervalent Iodine Compounds: Recent Advances in Synthetic Applications

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