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DOI: 10.1055/s-0040-1706034
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Late-Stage Functionalization

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

Florian Berger
,
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



Publication History

Received: 04 March 2021

Accepted after revision: 19 March 2021

Publication Date:
13 April 2021 (online)

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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