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Atom‐Economical Synthesis of Unsymmetrical Diaryl Selenides from Arylhydrazines and Diaryl Diselenides
Author(s) -
Taniguchi Toshihide,
Murata Akinori,
Takeda Motonori,
Mizuno Takumi,
Nomoto Akihiro,
Ogawa Akiya
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.201700938
Subject(s) - chemistry , homolysis , selenide , radical , aryl , combinatorial chemistry , radical nucleophilic aromatic substitution , organic chemistry , selenium , nucleophilic substitution , nucleophilic aromatic substitution , alkyl
An atom‐economical method for the synthesis of unsymmetrical diaryl selenides from arylhydrazines and stoichiometric amounts of diselenides was developed under mild conditions. The new and facile selenide synthesis involved the use of an inexpensive base in air to form unsymmetrical diaryl selenides in good yields. This C–Se radical arylation of diaryl diselenides was performed by forming aryl radicals from arylhydrazines under oxidative conditions. The formation of a phenyl radical was supported by trapping with 2,2,6,6‐tetramethylpiperidine‐1‐oxyl (TEMPO) in air. Therefore, this synthesis might involve a homolytic aromatic substitution (HAS) mechanism. The synthesis is both low costing and environmentally friendly and, therefore, may be useful for the practical synthesis of unsymmetrical diaryl selenides.