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

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

中文翻译：

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铜催化的二芳基碘鎓盐和腈的级联环状：含氮杂环的合成

摘要

开发通用的方法来构建各种含氮杂环是当代有机化学至关重要的组成部分。这篇综述总结了由二芳基碘鎓盐引发的含氮杂环形成的最新进展。在催化铜盐的存在下，二芳基碘鎓盐作为亲电子芳基化剂，可与腈反应生成高反应性物种N-芳基硝酸铵阳离子。这些物质可以与亲核试剂（包括C，N和O亲核试剂）有效反应，生成相应的产物。该策略不仅有效且方便，而且还能够合成各种含氮杂环，如喹啉，喹唑啉和菲啶。

1引言

2策略与机制

3级联

3.1芳环戊二烯，腈和C-亲核菌的级联环化

3.2芳环戊二烯，腈和N-亲核菌的级联环化

3.3级联二环戊二烯，腈和O-亲核菌的环化

4总结与展望

开发通用的方法来构建各种含氮杂环是当代有机化学至关重要的组成部分。这篇综述总结了由二芳基碘鎓盐引发的含氮杂环形成的最新进展。在催化铜盐的存在下，二芳基碘鎓盐作为亲电子芳基化剂，可与腈反应生成高反应性物种N-芳基硝酸铵阳离子。这些物质可以与亲核试剂（包括C，N和O亲核试剂）有效反应，生成相应的产物。该策略不仅有效且方便，而且还能够合成各种含氮杂环，如喹啉，喹唑啉和菲啶。

1引言

2策略与机制

3级联

3.1芳环戊二烯，腈和C-亲核菌的级联环化

3.2芳环戊二烯，腈和N-亲核菌的级联环化

3.3级联二环戊二烯，腈和O-亲核菌的环化

4总结与展望