Synlett 2024; 35(09): 1028-1032
DOI: 10.1055/s-0043-1763625
cluster
Chemical Synthesis and Catalysis in Germany

Regioselective Double C–H Functionalization of Arenes via Aryl Thianthrenium Salt Analogues

Aboubakr Hamad
a   Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
b   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
,
Michał Mrozowicz
a   Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
b   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
,
Yuanhao Xie
a   Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
,
Tobias Ritter
a   Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
› Author Affiliations
Open access funding provided by Max Planck Society.


Abstract

Directed C–H functionalization reactions are powerful tools for the rapid and selective syntheses of complex molecules. However, many existing C–H functionalization reactions require the presence of a preinstalled directing group that has to be either a part of the molecule or introduced onto an existing functional group. Here, we report analogues of thianthrene that can also function as directing groups for intermediate directed C–H functionalization and thereby permit regioselective 2,4- and 3,4-aromatic C–H difunctionalization of simple arenes in yields of 22–33% over three steps.

Supporting Information



Publication History

Received: 26 September 2023

Accepted after revision: 30 October 2023

Article published online:
27 November 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References and Notes

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