Intramolecular Benzyne–Phenolate [4+2] Cycloadditions. Issue 30 (8th May 2020)

• Record Type: Journal Article
• Authors: Takikawa, Hiroshi; Nishii, Arata; Takiguchi, Hiromu; Yagishita, Hirotoshi; Tanaka, Masato; Hirano, Keiichi; Uchiyama, Masanobu; Ohmori, Ken; Suzuki, Keisuke
• Is Part Of: Angewandte Chemie international edition. Volume 59:Issue 30(2020)
• Page Start: 12440
• Page End: 12444
• Publication Date: 2020-05-08
• Subjects: cycloaddition -- benzyne -- polycycles -- silicon -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202003131
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: An intramolecular benzyne–phenolate [4+2] cycloaddition is reported. Benzyne precursors, having vicinal halogen‐sulfonate functionalities, linked with a phenol(ate) by various tether groups undergo efficient intramolecular [4+2] cycloaddition by treatment with either Ph3 MgLi or n BuLi for halogen–metal exchange to form various benzobarrelenes. Abstract : An intramolecular benzyne–phenolate [4+2] cycloaddition has been developed. Benzyne precursors, having vicinal halogen‐sulfonate functionalities, linked with a phenol(ate) by various tether groups undergo efficient intramolecular [4+2] cycloaddition by treatment with either Ph3 MgLi or n BuLi, for halogen–metal exchange, to form various benzobarrelenes. The method is amenable to various reaction precursors and the products are isolated in high yield.