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Radical Aromatic Trifluoromethylthiolation: Photoredox Catalysis vs. Base Mediation
Author(s) -
Koziakov Denis,
Majek Michal,
Jacobi von Wangelin Axel
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701339
Subject(s) - chemistry , photoredox catalysis , radical , aryl , lipophilicity , catalysis , trifluoromethyl , yield (engineering) , base (topology) , photochemistry , combinatorial chemistry , organic chemistry , photocatalysis , mathematical analysis , alkyl , materials science , mathematics , metallurgy
Trifluoromethyl aryl sulfides (Ar‐SCF 3 ) constitute highly attractive building blocks due to their exceptional lipophilicity and chemical properties. Related protocols of radical aromatic trifluoro‐methylthiolation of arenediazonium salts were developed that are based on the facile generation of intermediate aryl radicals. Their reactions with commercial F 3 CS‐SCF 3 under very mild conditions afforded a diverse set of Ar‐SCF 3 (< 90 % yield). Direct comparison of photoredox catalysis {eosin Y or [Ru(bpy) 3 ]Cl 2 } with the weak base‐mediated dark reaction documented higher synthetic efficiency of the former but higher operational simplicity of the latter strategy.