The metal-free reaction between diazo compounds and boronic acids has been established in recent years as a powerful C(sp3)–C bond-forming reaction. This account covers the recent advances in this area. First, the various synthetic applications of reactions with N-sulfonylhydrazones as a convenient source of diazo compounds is discussed. These transformations can be regarded as reductive couplings of carbonyl compounds. Also covered is the incorporation of other mild sources of diazo compounds in these reactions: diazotization of amines and oxidation of hydrazones. Finally, the development of sequential and cascade processes is presented. 1 Introduction 2 Early Work: Reactions Between Alkylboranes and Diazo Compounds or N-Sulfonylhydrazones 2.1 Reactions Between Alkylboranes and Diazo Compounds 2.2 Reactions Between Alkylboranes and N-Sulfonylhydrazones 3 Reactions of N-Sulfonylhydrazones and Diazo Compounds with Aryl and Alkylboronic Acids 3.1 Reactions of Arylboroxines with Diazo Compounds 3.2 Reductive Couplings of N-Sulfonylhydrazones with Aryl- and Alkylboronic Acids 3.3 Three-Component Reactions Between α-Halotosylhydrazones, Boronic Acids and Indoles 4 Reactions of N-Tosylhydrazones with Alkenylboronic Acids 5 Synthesis of Allenes by Reactions with Alkynyl N-Nosylhydrazones 6 Reactions with Diazo Compounds Generated by Diazotization of Primary Amines 7 Reactions with Diazo Compounds Generated by Oxidation of ­Hydrazones 8 Reactions with Trimethylsilyldiazomethane 9 Cascade Cyclization Reactions with γ- and δ-Cyano-N-tosylhydrazones 10 Summary and Outlook

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硼酸与 N-磺酰腙或重氮化合物之间的无过渡金属反应：还原偶联过程及其他

近年来，重氮化合物与硼酸之间的无金属反应已被确立为一种强大的 C(sp3)–C 键形成反应。该帐户涵盖了该领域的最新进展。首先，讨论了与作为重氮化合物方便来源的 N-磺酰腙反应的各种合成应用。这些转化可视为羰基化合物的还原偶联。还包括在这些反应中加入其他温和的重氮化合物来源：胺的重氮化和腙的氧化。最后，介绍了顺序和级联过程的发展。1 引言 2 早期工作：烷基硼烷与重氮化合物或 N-磺酰腙之间的反应 2.1 烷基硼烷与重氮化合物之间的反应 2.