Rh(II)-catalyzed [2,3]-sigmatropic rearrangement of sulfur ylides derived from N-tosylhydrazones and sulfides

Li, Yuye; Huang, Zhongxing; Wu, Xinhu; Xu, Peng‐Fei; Jin, Jing; Zhang, Yan; Wang, Jianbo

doi:10.1016/j.tet.2012.03.032

Cited by 38 publications

(18 citation statements)

References 47 publications

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“…In this framework, tosylhydrazones are valuable precursors of unstabilised diazo compounds through the so-called Bamford–Stevens reaction. In the presence of catalytic Rh 2 (OAc) 4 and allyl sulfides, tosylhydrazones were transformed into sulfonium ylides able to undergo [2,3]-rearrangement [ 103 ]. Compared to previously reported methods, this approach allows for the formation of rearranged products without the requirement for an electron-withdrawing group usually necessary to stabilise the diazo starting material.…”

Section: Cascade Reactions Involving Transition Metal-catalysed Ylidementioning

confidence: 99%

Sulfur-Based Ylides in Transition-Metal-Catalysed Processes

et al. 2018

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Traditionally employed in the synthesis of small ring systems and rearrangement chemistry, sulfur-based ylides occupy a unique position in the toolbox of the synthetic organic chemist. In recent years a number of pioneering researchers have looked to expand the application of these unorthodox reagents through the use of transition metal catalysis. The strength and flexibility of such a combination have been shown to be of key importance in developing powerful novel methodologies. This chapter summarises recent developments in transition metal-catalysed sulfonium/sulfoxonium ylide reactions, as well as providing a historical perspective. In overviewing the successes in this area, the authors hope to encourage others into this growing field.

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Section: Cascade Reactions Involving Transition Metal-catalysed Ylidementioning

confidence: 99%

Sulfur-Based Ylides in Transition-Metal-Catalysed Processes

et al. 2018

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“…In this framework, tosylhydrazones are valuable precursors of unstabilised diazo compounds through the so-called Bamford-Stevens reaction. In the presence of catalytic Rh 2 (OAc) 4 and allyl sulfides, tosylhydrazones were transformed into Scheme 40 Enantioselective Doyle-Kirmse reaction under full catalyst control sulfonium ylides able to undergo [2,3]-rearrangement [103]. Compared to previously reported methods, this approach allows for the formation of rearranged products without the requirement for an electron-withdrawing group usually necessary to stabilise the diazo starting material.…”

Section: Scheme 32 Iron-catalysed Doyle-kirmse Reaction Of Allyl and mentioning

confidence: 99%

Sulfur-Based Ylides in Transition-Metal-Catalysed Processes

et al. 2018

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“…Eine solche Reaktion zur Bildung von Yliden kann auch in der Synthese der Homoallylsulfide 20 oder der 2,3‐Allenylsulfide 21 über die [2,3]‐sigmatrope Umlagerung des Ylid‐Intermediats 22 eingesetzt werden (Schema ) . Yu und Barluenga et al.…”

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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Rh(II)-catalyzed [2,3]-sigmatropic rearrangement of sulfur ylides derived from N-tosylhydrazones and sulfides

Cited by 38 publications

References 47 publications

Sulfur-Based Ylides in Transition-Metal-Catalysed Processes

Sulfur-Based Ylides in Transition-Metal-Catalysed Processes

Sulfur-Based Ylides in Transition-Metal-Catalysed Processes

Neue Ansätze für die Synthese von Metallcarbenen

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