A sustainable C–H functionalization of indoles, pyrroles and furans under a blue LED with iodonium ylides

Abstract

The pyrrole and indole derivatives are functionalized via a green initiative with dimethylmalonate derived phenyl iodonium ylide 4a in presence of blue LED via C-H functionalization of the respective heterocycles...

Transformations based on direct excitation of hypervalent iodine(iii) reagents

“…Sen reported a system in which different pyrrole and indole derivatives are functionalized with iodonium ylides under blue LEDs irradiation (Scheme 13A). 62 In their mechanism they propose an excitation of the EDA complexes between substrates and iodonium ylides, similarly as mentioned in the earlier report by Murphy and coworkers. 60 Lately, Li and Xuan reported a method for the synthesis of biologically relevant indolines through the cyclisation of tertiary aryl amines with iodonium ylides (Scheme 13B) under blue LEDs.…”

Direct Synthesis of Indolines via Cyclization of Tertiary Aryl Amines with Iodonium Ylides under Sole Visible Light Irradiation

“…Recently, Sen et al. realized the photochemical C−H functionalization of indoles, pyrroles and furans with iodonium ylides as dimethyl malonate fragment precursors (Scheme 1a) [14b] . Our group also developed a visible light‐promoted coupling of diazo compounds with iodonium ylides by using iodonium ylides as carbene trapping reagents [15] .…”

Three-Component Synthesis of Isoquinolone Derivatives via Rh(III)-Catalyzed C–H Activation and Tandem Annulation

“…Among them, iodonium ylides can be readily prepared from the corresponding active methylene compounds with iodobenzene diacetate and have been employed as a versatile synthon in synthetic organic chemistry due to their easy accessibility, good thermal stability, and rich reactivity . For instance, metal carbenoids can be generated via transition-metal-catalyzed facile decomposition of iodonium ylides, which are highly active intermediates in a wide variety of transformations such as C–H insertions, transylidations, as well as cyclizations (Scheme a). Moreover, iodonium ylides have also been utilized as carbene precursors in transition-metal-catalyzed C–H activation and cyclization reactions, providing a powerful approach for the rapid assembly of various cyclic or acrylic complex organic molecules (Scheme b) .…”