A hexameric resorcinarene capsule as a hydrogen bonding catalyst in the conjugate addition of pyrroles and indoles to nitroalkenes
文献信息
发布日期
2019-05-01
DOI
10.1039/C9QO00224C
影响因子
5.281
作者
Stefania Gambaro, Margherita De Rosa, Annunziata Soriente, Carmen Talotta, Giuseppe Floresta, Antonio Rescifina, Carmine Gaeta, Placido Neri
查看原文
摘要
A hexameric resorcinarene capsule acts as a hydrogen bonding catalyst for the activation of encapsulated nitroalkenes toward the addition of pyrroles and indoles. Once inside the capsule (C), β-nitrostyrene 3a establishes H-bonding interactions with the bridging water molecules having free H-bond-donating valences. Thus, the activation of nitroalkenes favors the conjugate addition of pyrroles and indoles. It is demonstrated that the inherent acidity of capsule C is sufficient to promote the Michael-type Friedel–Crafts (MTFC) reaction under the mild reaction conditions described herein. In silico calculations point out the catalytically relevant role of the bridging water molecules of C and confirm the supramolecular control exerted by the capsule, which protects the nitronic acid intermediate with respect to the degradation pathway that commonly occurs in the bulk medium.
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来源期刊
Organic Chemistry Frontiers
CiteScore:
7.8
自引率:
8.7%
年发文量:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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