Cu-Catalyzed Cascade Annulation of Diaryliodonium Salts and Nitriles: Synthesis of Nitrogen-Containing Heterocycles

Abstract

Developing versatile methodologies to construct various nitrogen­-containing heterocycles is a crucially significant part of contemporary organic chemistry. This review summarizes recent developments on the formation of nitrogen-containing heterocycles triggered by diaryliodonium salts. Diaryliodonium salts, as electrophilic arylating agents in the presence of catalytic copper salts, can react with nitriles to give N-arylnitrilium cations, which are highly reactive species. These species can efficiently react with nucleophiles, including C-, N- and O-nucleophiles, to give the corresponding products. This strategy is not only efficient and convenient, but also enables the synthesis of diverse nitrogen-containing heterocycles such as quinolines, quinazolines, and phenanthridines.

1 Introduction

2 Strategies and Mechanisms

3 Cascade Annulations

3.1 Cascade Annulation of Diaryliodoniums, Nitriles and C-Nucleo­philes

3.2 Cascade Annulation of Diaryliodoniums, Nitriles and N-Nucleo­philes

3.3 Cascade Annulation of Diaryliodoniums, Nitriles and O-Nucleo­philes

4 Summary and Outlook

Key words

diaryliodonium salts - nitriles - nitrogen-containing heterocycles - copper-catalyzed - cyclization

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