Recent progress in the application of iodonium ylides in organic synthesis

Abstract

Iodonium ylide has abstracted considerable attention due to its unique chemical properties and numerous applications as a versatile and sustainable reagent in organic synthesis. Therefore, great progress has been made...

Visible-Light-Induced Annulation of Iodonium Ylides and 2-Isocyanobiaryls to Access 6-Arylated Phenanthridines

“…Based on the above experimental results and the relevant reports, ,− we then proposed a tentative reaction mechanism for this visible-light-induced annulation reaction. As shown in Scheme , the photocatalyst 4-CzIPN ( PC ) is excited under irradiation of blue light to give the corresponding excited state PC* .…”

“…Iodonium ylides are recognized as a class of low-toxic, stable, and easy-handling building blocks for organic synthesis. They have been applied as carbene or carbenoid precursors in annulation reactions, C–H activation reactions, and difunctionalization of olefins . For example, they could be C1, C2, and C3 synthons in the Rh/Ru-catalyzed C–H activation/annulation reactions to furnish various heterocycles .…”

Coupling-Spirocyclization Cascade of Tryptamine-Derived Isocyanides with Iodonium Ylides and Despirocyclization Reactions

“…Until 2019, Liu and co-workers disclosed a Pd-catalyzed coupling and spirocyclization of diazo compounds with tryptamine-derived isocyanides, which provides a new strategy for the synthesis of spiroindoline compounds (Scheme b). Compared with diazo compounds, since carbene precursors are prone to be explosive, hypervalent iodine­(III) ylides (HVIs) seem more attractive in organic synthesis, because they are thermally more stable, inexpensive, and readily available . In recent years, HVIs-participated C-H functionalization reactions have been well-documented, in which metal carbene species were generated in situ with the help of transition-metal catalysts.…”

“…Compared with diazo compounds, since carbene precursors are prone to be explosive, hypervalent iodine(III) ylides (HVIs) seem more attractive in organic synthesis, because they are thermally more stable, inexpensive, and readily available. 9 In recent years, HVIs-participated C-H functionalization reactions have been well-documented, in which metal carbene species were generated in situ with the help of transition-metal catalysts. We also utilized iodonium ylides as carbene precursors to react with N-methoxy-1indolylformamide and constructed a series of indole-fused quinazolinone derivatives (Scheme 2c).…”

Copper(I) Iodide Catalyzed [3 + 3] Annulation of Iodonium Ylides with Pyridinium 1,4-Zwitterionic Thiolates for the Synthesis of 1,4-Oxathiin Scaffolds

“…Increasing the temperature to 80 °C in dichloroethane (DCE) resulted in the formation of a 36% yield of 1,4-oxathiin derivative 3aa . With the aim to work at milder reaction conditions, we decided to test iodonium ylides as carbene precursors, which are bench-stable, nontoxic, and easy to prepare from the corresponding 1,3-dicarbonyl compounds . 2-(Phenyl-λ 3 -iodanylidene)­cyclohexane-1,3-dione derivatives have also been tested as 3-atom synthons in [3 + 3] annulation reactions, especially in rhodium catalyzed cascades encompassing C–H activation with a directing group, carbene migratory insertion, and annulation .…”