Carbon Dioxide-Driven Palladium-Catalyzed C–H Activation of Amines: A Unified Approach for the Arylation of Aliphatic and Aromatic Primary and Secondary Amines

Mohit Kapoor; Pratibha Chand-Thakuri; Justin M. Maxwell; Daniel Liu; Hanyang Zhou; Michael C. Young

doi:10.1055/s-0037-1611381

Synlett, Inhaltsverzeichnis

Synlett 2019; 30(05): 519-524
DOI: 10.1055/s-0037-1611381

synpacts

Carbon Dioxide-Driven Palladium-Catalyzed C–H Activation of Amines: A Unified Approach for the Arylation of Aliphatic and Aromatic Primary and Secondary Amines

Mohit Kapoor

,

Pratibha Chand-Thakuri

,

Justin M. Maxwell

,

Daniel Liu

,

Hanyang Zhou

,

Michael C. Young *

Department of Chemistry and Biochemistry, School of Green Chemistry and Engineering, The University of Toledo, Toledo, OH, 43606, USA eMail: michael.young8@utoledo.edu

› Institutsangaben

Abstract

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Abstract

Amines are an important class of compounds in organic chemistry and serve as an important motif in various industries, including pharmaceuticals, agrochemicals, and biotechnology. Several methods have been developed for the C–H functionalization of amines using various directing groups, but functionalization of free amines remains a challenge. Here, we discuss our recently developed carbon dioxide driven highly site-selective γ-arylation of alkyl- and benzylic amines via a palladium-catalyzed C–H bond-activation process. By using carbon dioxide as an inexpensive, sustainable, and transient directing group, a wide variety of amines were arylated at either γ-sp³ or sp² carbon–hydrogen bonds with high selectivity based on substrate and conditions. This newly developed strategy provides straightforward access to important scaffolds in organic and medicinal chemistry without the need for any expensive directing groups.

1 Introduction

2 C(sp³)–H Arylation of Aliphatic Amines

3 C(sp²)–H Arylation of Benzylamines

4 Mechanistic Questions

5 Future Outlook

Key words

C–H activation - carbon dioxide - amines - sustainable chemistry - organometallics - synthetic methodology

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References

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