Felpin François-Xavier, Sengupta Saumitra
Université de Nantes, UFR des Sciences et des Techniques, CNRS UMR 6230, CEISAM, 2 rue de la Houssinière, 44322 Nantes Cedex 3, France.
Chemistry Consultant, 6/7 Central Park, Kolkata 700032, India.
Chem Soc Rev. 2019 Feb 18;48(4):1150-1193. doi: 10.1039/c8cs00453f.
The rich legacy of arenediazonium salts in the synthesis of unsymmetrical biaryls, built around the seminal works of Pschorr, Gomberg and Bachmann more than a century ago, continues to make important contributions at various evolutionary stages of modern biaryl synthesis. Based on in-depth mechanistic analysis and design of novel pathways and reaction conditions, the scope of biaryl synthesis with arenediazonium salts has enormously expanded in recent years through applications of transition metal/photoredox-catalysed cross-coupling, thermal/photosensitized radical chain CH-arylation of (hetero)arenes and arylative radical annulation reactions with alkynes. These recent developments have provided facile synthetic access to a wide variety of unsymmetrical biaryls of pharmaceutical, agrochemical and optoelectronic importance with green scale-up options and created opportunities for late-stage modification of peptides, nucleosides, carbon nanotubes and electrodes, the details of which are captured in this review.
一个多世纪前，基于普肖尔、贡伯格和巴赫曼的开创性工作，芳基重氮盐在不对称联芳基合成方面留下了丰富遗产，在现代联芳基合成的各个发展阶段持续做出重要贡献。基于深入的机理分析以及新型反应途径和反应条件的设计，近年来通过过渡金属/光氧化还原催化交叉偶联、（杂）芳烃的热/光敏自由基链CH-芳基化以及与炔烃的芳基化自由基环化反应，芳基重氮盐用于联芳基合成的范围已大幅扩展。这些最新进展为合成各种具有药物、农用化学品和光电子重要性的不对称联芳基化合物提供了简便途径，具有绿色放大的选择，并为肽、核苷、碳纳米管和电极的后期修饰创造了机会，本综述详述了其中的细节。
