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Ni/Ir‐Catalyzed Photoredox Decarboxylative Coupling of S‐Substituted Thiolactic Acids with Heteroaryl Bromides: Short Synthesis of Sulfoxaflor and Its SF 5 Analog
Author(s) -
Kanishchev Oleksandr S.,
Dolbier William R.
Publication year - 2017
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.201701627
Subject(s) - alkyl , chemistry , catalysis , combinatorial chemistry , coupling (piping) , coupling reaction , medicinal chemistry , stereochemistry , computational chemistry , organic chemistry , materials science , metallurgy
Metallaphotoredox cross‐coupling reactions have recently emerged as a powerful tool for the construction of C(sp 2 )−C(sp 3 ) bonds between alkyl chains and aromatic systems, including electron‐deficient heteroaryls, which are known to be challenging coupling partners. In this article, we disclose the Ni/Ir‐catalyzed photoredox decarboxylative coupling of readily available S‐substituted thiolactic acids with electron‐deficient heteroaryl bromides, which resulted in the formation of simple but otherwise not easily accessible heteroarenes with alkylsulfide side chains. To demonstrate a practical use of this coupling reaction, we have shown its efficiency in the one‐step synthesis of a key intermediate in the synthesis of the recently marketed insecticide Sulfoxaflor, and for the short synthesis of SF 5 ‐Sulfoxaflor.