Recent Advances on Radical-Mediated Cyanoalkylation/Cyanation using AIBN and Analogues as the Radical Sources

Abstract

AIBN (2,2′-azobisisobutyronitrile) and analogues are readily available chemical reagents that are widely used as free-radical initiators of polymer chemistry. Importantly, AIBN and derivatives are also safe and efficient (alkyl)cyano sources for synthesizing cyano-containing scaffolds. In the past decades, synthetic strategies using AIBN and derivatives as radical sources have attracted increasing attention from the synthetic community. This review will provide a valuable tool for understanding the importance of AIBN and derivatives in the area of synthetic chemistry. In this context, we present a comprehensive review that guides readers through the developments in AIBN chemistry over the past five years from several aspects.

1 Introduction

2 Radical Addition onto Alkenes or Alkynes using AIBN as Cyanoalkyl Radical

3 Dehydrogenated, decarboxylated cyano-alkylation by using AIBN and analogues

4 Synthesis of Ketone and its Derivatives with AIBN and Analogues as Carbonyl Source

5 Construction of Multi-ring Skeletons in the Presence of AIBN and Analogues

6 Direct Application as Cyano (CN) Source in Cyanation Reactions

7 Conclusions

Key words

AIBN and analogues - cyanoalkylation/cyanation - radical addition - C–H functionalization - radical initiator

Publication History

Received: 30 September 2022

Accepted after revision: 20 October 2022

Accepted Manuscript online:
20 October 2022

Article published online:
28 November 2022

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