A Direct Ylide Transfer to Carbonyl Derivatives and Heteroaromatic Compounds

Huang, Xueliang; Goddard, Richard; Maulide, Nuno

doi:10.1002/anie.201002919

Cited by 50 publications

(23 citation statements)

References 94 publications

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“…The intermolecular approach developed by Skrydstrup and co-workers led to the formation of various 2,4-disubstituted furans with good yields (Scheme 8) [25]. Investigations by Maulide and coworkers focussed on the gold-catalysed conversion of doubly-stabilised sulfonium ylides, prepared via a direct ylide transfer [26], into lactone-fused furan rings [27]. The efficiency of this intramolecular reaction was demonstrated on a wide range of substrates (Scheme 9).…”

Section: Transition Metals As π-Acid Catalystsmentioning

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: Transition Metals As π-Acid Catalystsmentioning

confidence: 99%

Sulfur-Based Ylides in Transition-Metal-Catalysed Processes

et al. 2018

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“…For example, Shen and co-workers reported the use of trifluoromethyl-substituted sulfonium ylide 5 in electrophilic trifluoromethylation reactions [ 33 – 34 ]. Moreover, Maulide and co-workers reported an effective ylide transfer reagent, which led to sulfonium ylide 6 [ 35 – 38 ].…”

Section: Introductionmentioning

confidence: 99%

“… The selected examples of sulfur(IV) and sulfur(VI) ylides 1 [ 1 ], 2 [ 5 – 7 ], 3 [ 6 – 7 9 ], 4 [ 11 – 12 ], 5 [ 33 – 34 ], 6 [ 35 – 38 ]. …”

Section: Introductionmentioning

confidence: 99%

One-pot sequential synthesis of tetrasubstituted thiophenes via sulfur ylide-like intermediates

Kim¹,

Lim²,

Jeong³

et al. 2018

Beilstein J. Org. Chem.

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Herein, we describe a novel approach for the practical synthesis of tetrasubstituted thiophenes 8. The developed method was particularly used for the facile preparation of thienyl heterocycles 8. The mechanism for this reaction is based on the formation of a sulfur ylide-like intermediate. It was clearly suggested by (i) the intramolecular cyclization of ketene N,S-acetals 7 to the corresponding thiophenes 8, (ii) 1 H NMR studies of Meldrum's acid-substituted aminothioacetals 9, and (iii) substitution studies of the methoxy group on Meldrum's acid containing N,S-acetals 9b. Notably, in terms of structural effects on the reactivity and stability of sulfur ylide-like intermediates, 2-pyridyl substituted compound 7a exhibited superior properties over those of others. 243

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“…teressanten Wechsel der Reaktivität aufdecken, bei dem Furanone mit quartären Kohlenstoffzentren entstehen, und den Mechanismus dieser Reaktionen mithilfe theoretischer Untersuchungen bestimmen. [7] Erste Studien konzentrierten sich auf das Alkin-substituierte Schwefel-Ylid 1 a, das durch einen direkten Ylid-Transfer [8] auf den entsprechenden Ketoester zugänglich ist. Die Reaktion dieser Verbindung mit verschiedenen Gold(I)-Verbindungen führte zu sehr unterschiedlichen Ergebnissen (siehe Hintergrundinformationen für Details), und wir konnten zeigen, dass die Behandlung mit kommerziell erhältlichem PPh 3 AuCl und AgSbF 6 bereits bei Raumtemperatur innerhalb von 3 Stunden quantitativ zum Furofuranon 2 a führt.…”

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“…Es ist wichtig anzumerken, dass alle Alkin-substituierten Schwefel-Ylid-Substrate durch einen einfachen, von uns beschriebenen Ylid-Transfer zugänglich sind. [8] Ihre Stabilität in der chromatographischen Aufarbeitung und der Umkristallisation, einhergehend mit ihrer hohen Kristallinität, macht sie zu einfach handhabbaren Substraten für weitere Transformationen.…”

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