Synthesis and esterification reactions of aryl diazomethanes derived from hydrazone oxidations catalyzed by TEMPO

Perusquia‐Hernandez, Carolina; Lara‐Issasi, Gonzalo R.; Frontana‐Uribe, Bernardo A.; Cuevas-Yáñez, Erick

doi:10.1016/j.tetlet.2013.04.079

Cited by 31 publications

(13 citation statements)

References 33 publications

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“…In our former work [19][20][21][22][23][24][25][26] , the two-step synthesis via hydrazones was reported to be a highly effective approach to obtain aryldiazomethanes. However, it was of interest to examine the reaction of bis(aryldiazomethane)s as compared to mono(aryldiazomethane)s, and for that purpose, acetic acid was used to react with bis(aryldiazomethane), a known very fast reaction used to generate esters 31,32 . From the IR spectra, NMR spectra, and MS data, the structures of bis(arylester)s products 4a~e were confirmed, and no mono(arylester)s were formed.…”

Section: Synthesis and Characterization Of Bis(aryldiazomethane)smentioning

confidence: 99%

Surface modification of polymers with bis(arylcarbene)s from bis(aryldiazomethane)s: preparation, dyeing and characterization

Yang

Moloney

2016

RSC Adv.

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Section: Synthesis and Characterization Of Bis(aryldiazomethane)smentioning

confidence: 99%

Surface modification of polymers with bis(arylcarbene)s from bis(aryldiazomethane)s: preparation, dyeing and characterization

Yang

Moloney

2016

RSC Adv.

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“…α‐Diazo carbonyl compounds are more stable than alkyl diazos, but the diazo functional group is typically not carried through long synthetic sequences due to reactivity concerns. Incorporating a diazo group into a complex molecule is not always trivial, and is most often achieved by diazo transfer to a carbonyl enolate, or the oxidation of a hydrazine‐based precursor . In view of their synthetic utility, alternative strategies to prepare structurally complex diazo‐containing compounds would be beneficial to the synthetic community.…”

Section: Methodsmentioning

confidence: 99%

A Conjugate Addition Approach to Diazo‐Containing Scaffolds with β Quaternary Centers

2020

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Structurally complex diazo‐containing scaffolds are formed by conjugate addition to vinyl diazonium salts. The electrophile, a little studied α‐diazonium‐α,β‐unsaturated carbonyl compound, is formed at low temperature under mild conditions by treating β‐hydroxy‐α‐diazo carbonyls with Sc(OTf)3. Conjugate addition occurs selectively at the 3‐position of indole to give α‐diazo‐β‐indole carbonyls, and enoxy silanes react to give 2‐diazo‐1,4‐dicarbonyl products. These reactions result in the formation of tertiary and quaternary centers, and give products that would be otherwise difficult to form. Importantly, the diazo functional group is retained within the molecule for future manipulation. Treating an α‐diazo ester indole addition product with Rh2(OAc)4 caused a rearrangement to occur to give a 2‐(1H‐indol‐3‐yl)‐2‐enoate. In the case of diazo ketone compounds, this shift occurred spontaneously on prolonged exposure to the Lewis acidic reaction conditions.

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“…beobachteten außerdem Carbendimerisierungen bei der Oxidation von Hydrazonen, die mit bemerkenswerten Z/E ‐Selektivitäten abliefen . Andere Arten von Reaktionen, wie O‐H‐Insertionen von Carbonsäuren, wurden ebenfalls beschrieben ,…”

Section: Hydrazoneunclassified

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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Synthesis and esterification reactions of aryl diazomethanes derived from hydrazone oxidations catalyzed by TEMPO

Cited by 31 publications

References 33 publications

Surface modification of polymers with bis(arylcarbene)s from bis(aryldiazomethane)s: preparation, dyeing and characterization

Surface modification of polymers with bis(arylcarbene)s from bis(aryldiazomethane)s: preparation, dyeing and characterization

A Conjugate Addition Approach to Diazo‐Containing Scaffolds with β Quaternary Centers

Neue Ansätze für die Synthese von Metallcarbenen

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