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DOI: 10.1055/s-0040-1706034
Site-Selective Late-Stage C–H Functionalization via Thianthrenium Salts
We thank the Max-Planck-Instititut für Kohlenforschung, Mülheim an der Ruhr and UCB Biopharma for funding.
Abstract
The high abundance of C–H bonds in organic molecules makes C–H functionalization a powerful approach to quickly increase the complexity of an organic molecule. However, the high abundance of C–H bonds also provides a challenge to C–H functionalization reactions: selectivity. While most C–H functionalization reactions produce mixtures of different products for most substrates, we have developed a highly selective method for aromatic C–H functionalization via sulfonium salts. The reaction does not require a certain directing group to be selective. The introduced functional group is a sulfonium group, which participates in various follow-up reactions such as palladium-catalyzed cross-coupling reactions and photoredox catalysis. Here we discuss our pathway to develop the reaction as well as its scope and utility.
1 Introduction
2 Site-Selective Synthesis of Sulfonium Salts
3 Sulfonium Salts in Palladium-Catalyzed Cross-Coupling
4 Sulfonium Salts in Photoredox Catalysis
5 Sulfur(IV) Reductive Elimination
6 Cine Substitution
7 Conclusion
Key words
C–H functionalization - selectivity - sulfonium salts - cross-coupling - photoredox catalysisPublication History
Received: 04 March 2021
Accepted after revision: 19 March 2021
Article published online:
13 April 2021
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