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Synthesis, Structure, and Reactivity of 5‐(Aryl)dibenzothiophenium Triflates
Author(s) -
Kafuta Kevin,
Korzun André,
Böhm Marvin,
Golz Christopher,
Alcarazo Manuel
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201912383
Subject(s) - aryl , chemistry , dibenzothiophene , reactivity (psychology) , combinatorial chemistry , coupling reaction , sequence (biology) , oxide , scope (computer science) , organic chemistry , catalysis , computer science , medicine , biochemistry , alkyl , alternative medicine , pathology , programming language
A synthetic protocol for the preparation of 5‐(aryl)dibenzothiophenium salts starting from inexpensive dibenzothiophene S ‐oxide and simple arenes is reported. The scope of the method regarding the nature of the arene is evaluated, intermediates along the reaction sequence have been trapped, and side‐reactions identified. In addition, the X‐ray structures of a complete set of these salts are reported and their reactivities studied. Specifically, chemoselective Suzuki coupling is observed at the dibenzothiophenium in the presence of iodides.