A direct and efficient 3-halooxidation of indoles using DMSO as oxygen source

Tao Zheng, Zhiqun Li,Yuling Luo,Jingjie Zhang,Jun Xu

Tetrahedron(2023)

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Abstract
Here we develop a direct and efficient protocol for 3-halooxidation of indoles using DMSO as the oxygen source and NXS (X 1/4 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 SN1 substitution of a highly reactive electrophilic o-azaxylylene intermediate to generate 3, 3-disubstituted oxindoles. (c) 2023 Elsevier Ltd. All rights reserved.
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Key words
3-Halooxidation,Atom -economical,S N 1 substitution,O-azaxylylene intermediate,3-Disubstituted oxindole
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