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Two‐Step Synthesis of Unsymmetrical Diaryl Sulfides by Electrophilic Thiolation of Non‐functionalized (Hetero)arenes
Author(s) -
Böhm Marvin J.,
Golz Christopher,
Rüter Isabelle,
Alcarazo Manuel
Publication year - 2018
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.201802806
Subject(s) - electrophile , reagent , combinatorial chemistry , chemistry , grignard reagent , modular design , reaction conditions , organic chemistry , computer science , catalysis , operating system
This article reports the efficient preparation of a series of unsymmetrically substituted thioethers through a two‐step procedure consisting of an initial metal‐free C−H sulfenylation of electron‐rich (hetero)arenes with newly prepared succinylthioimidazolium salts. Subsequent reaction of the arylthioimidazolium intermediates with Grignard reagents afford the desired thioethers. The synthetic protocol described is modular, scalable, and high yielding, and provides access to sulfides that are not easy to obtain through the existing methodologies. Importantly, no prefunctionalization of the initial (hetero)arene is required.