Direct Arylation of C(sp2)–H Bonds in Anilines

Clément Jacob; Julien Annibaletto; Bert U. W. Maes; Gwilherm Evano

doi:10.1055/a-2039-7985

Synthesis, Table of Contents

Synthesis 2023; 55(12): 1799-1823
DOI: 10.1055/a-2039-7985

review

Direct Arylation of C(sp²)–H Bonds in Anilines

Clément Jacob∗

^aLaboratoire de Chimie Organique, Service de Chimie et Physico-Chimie Organiques, Université Libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/6, 1050 Brussels, Belgium

^bOrganic Synthesis Division, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium

,

Julien Annibaletto

^aLaboratoire de Chimie Organique, Service de Chimie et Physico-Chimie Organiques, Université Libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/6, 1050 Brussels, Belgium

,

Bert U. W. Maes

^bOrganic Synthesis Division, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium

,

Gwilherm Evano ∗

^aLaboratoire de Chimie Organique, Service de Chimie et Physico-Chimie Organiques, Université Libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/6, 1050 Brussels, Belgium

› Author Affiliations

Abstract

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Abstract

Anilines selectively arylated at their ortho, meta or para positions are useful building blocks in synthesis and have found applications in many areas. The most straightforward method for their synthesis relies on the direct arylation of a C(sp²)–H bond of anilines, an attractive strategy avoiding the prefunctionalization of the starting anilines provided that such arylations proceed with high levels of regioselectivity. Such reactions are presented and discussed, in a comprehensive manner, in this review article, with an emphasis on the regioselectivity of the processes and factors governing both the reactivity and selectivity.

1 Introduction

2 ortho-Arylation of Anilines

2.1 Direct C(sp²)–H ortho-Arylation of Anilines

2.2 Directed C(sp²)–H ortho-Arylation of Anilines

3 meta-Arylation of Anilines

4 para-Arylation of Anilines

4.1 Direct C(sp²)–H para-Arylation of Anilines via Oxidative Radical Homodimerization

4.2 Direct C(sp²)–H para-Arylation of Anilines via Transition-Metal Catalysis

5 Conclusion and Outlook

Key words

anilines - C–H arylation - regioselectivity - catalysis - directing groups

Full Text

References

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