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Visible‐Light Promoted Catalyst‐Free Imidation of Arenes and Heteroarenes
Author(s) -
Song Lu,
Zhang Long,
Luo Sanzhong,
Cheng JinPei
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201404479
Subject(s) - regioselectivity , homolysis , catalysis , chemistry , photochemistry , visible spectrum , electron transfer , cleavage (geology) , irradiation , radical , combinatorial chemistry , organic chemistry , materials science , physics , optoelectronics , fracture (geology) , nuclear physics , composite material
Abstract We described herein a catalyst‐free visible‐light photolytic protocol for the imidation of arenes and heteroarenes. N‐Bromosaccharin was identified as a viable and chemoselective nitrogen radical precursor that undergoes controllable homolytic cleavage under ambient light irradiation. The reaction can be applied to a number of arenes and heteroarenes with good chemo‐ and regioselectivity. Mechanistic studies revealed that radical chain termination by electron transfer‐proton transfer (ET‐PT) is the leading productive pathway for the reaction.