Sulfonylation of 1,4‐Diazabicyclo[2.2.2]octane: Charge‐Transfer Complex Triggered C−N Bond Cleavage

A novel charge‐transfer complex triggered sulfonylation of 1,4‐diazabicyclo[2.2.2]octane (DABCO) with mild reaction conditions has been developed. The formation of a charge‐transfer complex between electron‐withdrawing (hetero)aryl sulfonyl chloride and DABCO allows the synthesis of N‐ethylated pipe...

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Detalles Bibliográficos
Autores principales: Fu, Ying, Xu, Qin‐Shan, Li, Quan‐Zhou, Li, Ming‐Peng, Shi, Chun‐Zhao, Du, Zhengyin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6350051/
https://www.ncbi.nlm.nih.gov/pubmed/30723657
http://dx.doi.org/10.1002/open.201800251
Descripción
Sumario:A novel charge‐transfer complex triggered sulfonylation of 1,4‐diazabicyclo[2.2.2]octane (DABCO) with mild reaction conditions has been developed. The formation of a charge‐transfer complex between electron‐withdrawing (hetero)aryl sulfonyl chloride and DABCO allows the synthesis of N‐ethylated piperazine sulfonamide in good yields. The reaction has a high functional group tolerance. Spectroscopic studies confirmed the charge‐transfer complex formation between sulfonyl chlorides and DABCO, which facilitates the C−N bond cleavage of DABCO.

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