Merging the Reactivity of (Pseudo)cyclic Hypervalent Iodine Reagents and Carbenes or Carbenoids

Abstract In this short review, we present applications merging the reactivity of cyclic hypervalent iodine reagents with carbenes and carbenoids developed in the period 2014–2024. The use of more stable cyclic hypervalent iodine reagents has led to major advances in this area. The combination of iodine(III) chemistry with carbenes or carbenoids enables new disconnections that are not possible using classical reactivity. Both the use of hypervalent iodine compounds as partners in reactions with metal carbenes and as reagents combining the reactivity of iodine(III) and carbenes in a single molecule to give carbyne equivalents are discussed in this review. 1 Introduction 2 Transfer of Fluorinated Groups (F, CF3) 3 Oxy- and Aminoalkyn(en)ylation 3.1 Oxy- and Aminoalkynylation with Acceptor-Substituted Diazo Compounds 3.2 Oxyalkenylation with Acceptor-Substituted Diazo Compounds 3.3 Oxyalkynylation with Acceptor-Acceptor-Substituted Diazo Compounds 4 Carbyne Equivalents 4.1 Diazo-Based Reagents 4.2 Sulfur Ylide Based Reagents 5 Conclusion