A direct and efficient 3-halooxidation of indoles using DMSO as oxygen source. (3rd March 2023)

• Record Type: Journal Article
• Authors: Zheng, Tao; Li, Zhiqun; Luo, Yuling; Zhang, Jingjie; Xu, Jun
• Is Part Of: Tetrahedron. Volume 133(2023)
• Publication Date: 2023-03-03
• Subjects: 3-Halooxidation -- Atom-economical -- SN1 substitution -- O-azaxylylene intermediate -- 3, 3-Disubstituted oxindole; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2023.133274
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Here we develop a direct and efficient protocol for 3-halooxidation of indoles using DMSO as the oxygen source and NXS (X = Br, Cl) the halo source. This protocol features broad substrate scope and good to excellent yields, thus rendering it as a highly versatile, straightforward, and atom-economical alternative prior to the previously reported methods, which possess their capability to undergo the SN 1 substitution of a highly reactive electrophilic o -azaxylylene intermediate to generate 3, 3-disubstituted oxindoles. Graphical abstract: Image 1