[3+2]-Cycloaddition reactions of 2-phenyliodonio-5,5-dimethyl-1,3-dioxacyclohexanemethylide

Gogonas, Efstathios P.; Hadjiarapoglou, Lazaros P.

doi:10.1016/s0040-4039(00)01672-5

Cited by 52 publications

(23 citation statements)

References 25 publications

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“…23 Notably, the rhodium catalysed transformation proceeded with higher yields than the analogous Cu(II)-catalysed process. 23 Notably, the rhodium catalysed transformation proceeded with higher yields than the analogous Cu(II)-catalysed process.…”

Section: Scheme 12 Rh(ii)-catalysed Synthesis Of Oxazoles 38mentioning

confidence: 99%

Transition Metal-Mediated Synthesis of Oxazoles

Bresciani¹,

Tomkinson²

2014

HETEROCYCLES

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Among the synthetic methods for the formation of the oxazole ring, transition metal-mediated protocols are the most attractive in terms of selectivity, efficiency and mildness of reaction conditions. In this review we discuss methods for the preparation of oxazoles using transition metal complexes highlighting the key bonds being formed. This reveals critical gaps in the existing literature for the construction of this biologically significant ring system highlighting exciting opportunities for further research.

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Section: Scheme 12 Rh(ii)-catalysed Synthesis Of Oxazoles 38mentioning

confidence: 99%

Transition Metal-Mediated Synthesis of Oxazoles

Bresciani¹,

Tomkinson²

2014

HETEROCYCLES

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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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“…Iodonium ylides can be converted to singlet carbenes under irradiation using a mercury (Hg) lamp, and the groups of Hadjiarapoglou, Matveeva, and Spyroudis have reported examples of cyclopropanation and related cycloaddition events. These reactions thus proceed via free carbenes, which are formed upon cleavage of the ylide C−IPh bond, but the heat generated by the lamp is often an unavoidable source of technical complications and chemical selectivity issues.…”

Section: Introductionmentioning

confidence: 99%

Blue LED Irradiation of Iodonium Ylides Gives Diradical Intermediates for Efficient Metal‐free Cyclopropanation with Alkenes

et al. 2019

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A facile and highly chemoselective synthesis of doubly activated cyclopropanes is reported where mixtures of alkenes and β‐dicarbonyl‐derived iodonium ylides are irradiated with light from blue LEDs. This metal‐free synthesis gives cyclopropanes in yields up to 96 %, is operative with cyclic and acyclic ylides, and proceeds with a variety of electronically‐diverse alkenes. Computational analysis explains the high selectivity observed, which derives from exclusive HOMO to LUMO excitation, instead of free carbene generation. The procedure is operationally simple, uses no photocatalyst, and provides access in one step to important building blocks for complex molecule synthesis.

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[3+2]-Cycloaddition reactions of 2-phenyliodonio-5,5-dimethyl-1,3-dioxacyclohexanemethylide

Cited by 52 publications

References 25 publications

Transition Metal-Mediated Synthesis of Oxazoles

Transition Metal-Mediated Synthesis of Oxazoles

Neue Ansätze für die Synthese von Metallcarbenen

Blue LED Irradiation of Iodonium Ylides Gives Diradical Intermediates for Efficient Metal‐free Cyclopropanation with Alkenes

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