The structure of McN-5652

Viele moderne organische Synthesen nutzen die intrinsische, natürliche Polarität der chemischen Bindungen und reaktiven Zentren der Substrate. Die Entwicklung unkonventionell polarisierter Synthone ist daher eine wünschenswerte Strategie, weil somit neuartige retrosynthetische Schritte in der Synthese komplexer Strukturen zugänglich gemacht werden können. Während die Umpolung von Carbonylzentren eine gängige Strategie ist, finden sich in der Literatur nur wenige Berichte über die Polaritätsumkehr der α‐Position von Carbonylen. Wir stellen hier die Entwicklung einer neuen elektrophilen Enoloniumspezies und ihre Anwendung in der chemoselektiven, metallfreien oxidativen C‐C‐Kupplung vor.

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Metallfreie formale oxidative C‐C‐Kupplung durch In‐situ‐Erzeugung einer elektrophilen Enoloniumspezies

Kaiser

Torre

Shaaban

et al. 2017

Angewandte Chemie

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Metal‐Free Formal Oxidative C−C Coupling by In Situ Generation of an Enolonium Species

et al. 2017

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Much contemporary organic synthesis relies on transformations that are driven by the intrinsic, so-called "natural", polarity of chemical bonds and reactive centers. The design of unconventionally polarized synthons is a highly desirable strategy, as it generally enables unprecedented retrosynthetic disconnections for the synthesis of complex substances. Whereas the umpolung of carbonyl centers is a well-known strategy, polarity reversal at the α-position of a carbonyl group is much rarer. Herein, we report the design of a novel electrophilic enolonium species and its application in efficient and chemoselective, metal-free oxidative C-C coupling.

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Inhibition of serotonin transport by (+)McN5652 is noncompetitive

Hummerich¹,

Schulze²,

Rädler³

et al. 2006

Nuclear Medicine and Biology

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The structure of McN-5652

Cited by 5 publications

References 8 publications

Metallfreie formale oxidative C‐C‐Kupplung durch In‐situ‐Erzeugung einer elektrophilen Enoloniumspezies

Metallfreie formale oxidative C‐C‐Kupplung durch In‐situ‐Erzeugung einer elektrophilen Enoloniumspezies

Metal‐Free Formal Oxidative C−C Coupling by In Situ Generation of an Enolonium Species

Inhibition of serotonin transport by (+)McN5652 is noncompetitive

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