Intramolecular Benzyne–Phenolate [4+2] Cycloadditions
Hiroshi Takikawa, Arata Nishii, Hiromu Takiguchi, Hirotoshi Yagishita, Masato Tanaka, Keiichi Hirano, Masanobu Uchiyama, Ken Ohmori, Keisuke Suzuki
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 Ph 3 MgLi or n BuLi for halogen–metal exchange to form various benzobarrelenes.
Topics & Concepts
AryneIntramolecular forceCycloadditionVicinalChemistryHalogenMedicinal chemistryStereochemistryOrganic chemistryCatalysisAlkylCyclization and Aryne ChemistryCatalytic Alkyne ReactionsChemical Reactions and Mechanisms