Intramolecular Ynamide–Benzyne (3+2) Cycloadditions. (3rd April 2023)

• Record Type: Journal Article
• Authors: Tawatari, Tsukasa; Kato, Ritsuki; Kudo, Riku; Takasu, Kiyosei; Takikawa, Hiroshi
• Is Part Of: Angewandte Chemie. Volume 135:Number 19(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2023-04-03
• Subjects: Benzyne -- Cycloaddition -- Heterocycles -- Ylides -- Ynamides; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202300907
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: We report herein intramolecular (3+2) cycloaddition reactions between ynamides as three‐atom components and benzyne. In these intramolecular reactions, the two‐bond formation is realized by exploiting benzyne precursors that contain a chlorosilyl group as a linking functionality. This method thus highlights the ambivalent character of the intermediate indolium ylide, which exhibits both nucleophilic and electrophilic properties at its C2 atom. Abstract : Intramolecular (3+2) cycloaddition reactions involving benzyne and ynamides as three‐atom components have been accomplished through the utilization of benzyne precursors having a linking functionality. The ambivalent nature of the intermediate indolium ylide, which exhibits both nucleophilic and electrophilic properties at its C2 atom, is thus brought to light in this approach.