Chalcogen Bonding Catalysis of a Nitro‐Michael Reaction

Abstract: Chalcogen bonding is the non‐covalent interaction between Lewis acidic chalcogen substituents and Lewis bases. Herein, we present the first application of dicationic tellurium‐based chalcogen bond donors in the nitro‐Michael reaction between trans‐β‐nitrostyrene and indoles. This also constitutes the first activation of nitro derivatives by chalcogen bonding (and halogen bonding). The catalysts showed rate accelerations of more than a factor of 300 compared to strongly Lewis acidic hydrogen bond donors. Several comparison experiments, titrations, and DFT calculations support a chalcogen‐bonding‐based mode of activation of β‐nitrostyrene.

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• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

• Bibliographic citation: Chalcogen Bonding Catalysis of a Nitro‐Michael Reaction ; volume:58 ; number:47 ; year:2019 ; pages:16923-16927 ; extent:5 ; Angewandte Chemie / International edition. International edition ; 58, Heft 47 (2019), 16923-16927 (gesamt 5)

Contributors, Places and Time

• Creator: Wonner, Patrick ; Dreger, Alexander ; Vogel, Lukas ; Engelage, Elric ; Huber, Stefan M.

Further information

• DOI: 10.1002/anie.201910639
• URN: urn:nbn:de:101:1-2022071211012108592712
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.