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Visible‐Light‐Driven Remote C−H Chlorination of Aliphatic Sulfonamides with Sodium Hypochlorite
Author(s) -
Zhu Yanshuo,
Wang JuanJuan,
Wu Danhua,
Yu Wei
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000354
Subject(s) - chemistry , sodium hypochlorite , yield (engineering) , hypochlorite , visible spectrum , catalysis , tandem , photochemistry , organic chemistry , medicinal chemistry , materials science , physics , optoelectronics , metallurgy , composite material
The C(sp 3 )−H chlorination of aliphatic sulfonamides was realized by visible‐light photoredox catalysis with Ru(bpy) 3 Cl 2 as photocatalsyt and NaOCl⋅5H 2 O crystals as the chlorinating agent. The reaction proceeds in a tandem pattern of N−H chlorination and Hofmann‐Löffler‐Freytag chlorination. A variety of differently substituted sulfonamides were chlorinated in this way in high yield. A radical‐chain mechanism is proposed for the reaction on the basis of experimental evidence.