Site-Selective Late-Stage C–H Functionalization via Thianthrenium Salts

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 catalysis

Publication History

Received: 04 March 2021

Accepted after revision: 19 March 2021

Article published online:
13 April 2021

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