Synthesis, Structure, and Reactivity of 5‐(Aryl)dibenzothiophenium Triflates. Issue 5 (26th November 2019)

• Record Type: Journal Article
• Authors: Kafuta, Kevin; Korzun, André; Böhm, Marvin; Golz, Christopher; Alcarazo, Manuel
• Is Part Of: Angewandte Chemie international edition. Volume 59:Issue 5(2020)
• Page Start: 1950
• Page End: 1955
• Publication Date: 2019-11-26
• Subjects: cross-coupling -- palladium -- structure elucidation -- sulfur -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201912383
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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. Abstract : Easy on, easy off : 5‐(aryl)dibenzothiophenium triflates were prepared by highly selective metal‐free C−H sulfenylation of arenes. Interestingly, these salts undergo site‐selective Suzuki–Miyaura coupling in the presence of C−I bonds, enabling the iterative synthesis of polyaromatics.