Construction of 2, 3-quaternary fused indolines from alkynyl tethered oximes and diaryliodonium salts through a cascade strategy of N-arylation/cycloaddition/[3, 3]-rearrangement. Issue 24 (14th November 2017)

• Record Type: Journal Article
• Authors: Ma, Xiao-Pan; Li, Kun; Wu, Si-Yi; Liang, Cui; Su, Gui-Fa; Mo, Dong-Liang
• Is Part Of: Green chemistry. Volume 19:Issue 24(2017)
• Page Start: 5761
• Page End: 5766
• Publication Date: 2017-11-14
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/c7gc02844j
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : An efficient cascade strategy was developed for the synthesis of 2, 3-quaternary fused indolines from alkynyl tethered oximes and diaryliodonium salts. Abstract : A variety of 2, 3-quaternary fused indolines could be prepared in good yields with high diastereoselectivity from alkynyl tethered oximes and diaryliodonium salts under mild metal-free conditions. The reaction initially goes through a selective N -arylation to provide alkynyl tethered nitrones and regioselectively undergoes an intramolecular (3 + 2) cycloaddition followed by a [3, 3]-sigmatropic rearrangement to afford 2, 3-quaternary fused indolines in a one-pot fashion. The method features easily available cheap materials, multiple bond formation, gram scalable preparation and diversity of fused indoline scaffolds.