Synlett 2018; 29(15): 1937-1943
DOI: 10.1055/s-0037-1610150
synpacts
© Georg Thieme Verlag Stuttgart · New York

The Direct Pd-Catalyzed β-C(sp3)–H Activation of Carboxylic Acids

Alexander Uttry
a  Westfälische Wilhelms-Universität-Münster, Corrensstr. 40, 48149 Münster, Germany   Email: mvangemmeren@uni-muenster.de
,
Manuel van Gemmeren*
a  Westfälische Wilhelms-Universität-Münster, Corrensstr. 40, 48149 Münster, Germany   Email: mvangemmeren@uni-muenster.de
b  Max Planck Institute for Chemical Energy Conversion, Stiftstr. 34–36, 45470 Mülheim an der Ruhr, Germany
› Author Affiliations
We thank Max Planck Society (Otto Hahn Award to M.v.G.), the Fonds der Chemischen Industrie (Liebig Fellowship to M.v.G.), the WWU Münster, and the SFB858 for financial support.

Further Information

Publication History

Received: 20 March 2018

Accepted after revision: 20 April 2018

Publication Date:
23 May 2018 (online)

Abstract

The carboxylic acid moiety is one of the most versatile and abundant functional groups. However, despite of tremendous progress in the field of C–H functionalization reactions its use as a directing group for C(sp3)–H activation has remained limited. In this Synpact article we present the challenges associated with the carboxylic acid moiety as a native directing group and report on the newest developments in this field, including our recent study in which we developed a generally applicable protocol for the direct palladium catalyzed β-C(sp3)–H arylation of propionic acid and related α-branched aliphatic acids giving access to hydrocinnamic acids derivatives in a highly straightforward manner.

1 Introduction

2 Challenges in the C(sp3)–H Bond Activation of Carboxylic Acids

3 History/State of the Art

4 Studies towards a General β-C(sp3)–H Functionalization of ­Aliphatic Acids

5 Conclusion

 
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