Benzyne 1,2,4-Trisubstitution and Dearomative 1,2,4-Trifunctionalization
Jiarong Shi, Lianggui Li, Chunhui Shan, Zhonghong Chen, Liang Dai, Min Tan, Yu Lan, Yang Li
Abstract
Both 1,2,4-trisubstitution and dearomative 1,2,4-trifunctionalization of benzyne have been accomplished from sulfoxides bearing a penta-2,4-dien-1-yl moiety. These cascade transformations proceed through a benzyne insertion into the S═O bond and an uncommon regiospecific anionic [4,5]-sigmatropic rearrangement, furnishing a C-O, C-S, and C-C bond on the C1-, C2-, and C4-position of a benzene ring, respectively. This study showcases new cascade benzyne reaction modes involving both distal C-H bond functionalization and dearomatization.
Topics & Concepts
AryneChemistryMoietyRing (chemistry)BenzeneStereochemistryMedicinal chemistrySigmatropic reactionCascadeOrganic chemistryChromatographyCyclization and Aryne ChemistryCatalytic Alkyne ReactionsOrganic Chemistry Cycloaddition Reactions