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Room‐Temperature C‐H Bromination and Iodination with Sodium Bromide and Sodium Iodide Using N ‐Fluorobenzenesulfonimide as an Oxidant
Author(s) -
Shi Cuiying,
Miao Qi,
Ma Lifang,
Lu Tao,
Yang Dong,
Chen Jiaming,
Li Ziyuan
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201901456
Subject(s) - halogenation , chemistry , sodium iodide , sodium bromide , halide , halogen , sodium , iodide , bromide , regioselectivity , combinatorial chemistry , organic chemistry , catalysis , alkyl
A transition‐metal‐free electrophilic bromination and iodination of arene through C−H cleavage at room temperature has been developed in excellent to quantitative yields with broad arene scope and good regioselectivity, in which environment‐benign and readily available sodium halides, NaBr or NaI, were employed as halogen sources in accompany with N ‐fluorobenzenesulfonimide (NFSI) as an oxidant. Studies have also demonstrated that, in this air‐ and moisture‐resistant scalable halogenation under mild conditions, the oxidant NFSI is reduced to dibenzenesulfonimide which usually serves as the starting material for the preparation of NFSI, rendering this facile and versatile protocol promising potentials for future applications in organic synthesis.