Palladium-Catalyzed Organic Reactions Involving Hypervalent Iodine Reagents

Abstract

The chemistry of polyvalent iodine compounds has piqued the interest of researchers due to their role as important and flexible reagents in synthetic organic chemistry, resulting in a broad variety of useful organic molecules. These chemicals have potential uses in various functionalization procedures due to their non-toxic and environmentally friendly properties. As they are also strong electrophiles and potent oxidizing agents, the use of hypervalent iodine reagents in palladium-catalyzed transformations has received a lot of attention in recent years. Extensive research has been conducted on the subject of C—H bond functionalization by Pd catalysis with hypervalent iodine reagents as oxidants. Furthermore, the iodine(III) reagent is now often used as an arylating agent in Pd-catalyzed C—H arylation or Heck-type cross-coupling processes. In this article, the recent advances in palladium-catalyzed oxidative cross-coupling reactions employing hypervalent iodine reagents are reviewed in detail.

Applications of Phenyliodine(III)diacetate in C−H Functionalization and Hetero‐Hetero Bond Formations: A Septennial Update

“…[80] An atom-efficient one-pot synthesis of novel push-pull dienaminodiones (12) was disclosed by Lankalapalli and his group, using indoles (9) and a Schiff base generated from 3,4dihydroxysalicylaldehyde (10) in the presence of PIDA (Scheme 1). [81] A wide range of indoles and anilines (11) made up the broad substrate scope of the methodology with good to moderate yields. The proposed approach functioned as a sequential multicomponent reaction since the formation of Schiff base was followed by an addition of indole to produce dienaminodione in one-pot.…”

Catalytic stereoselective synthesis involving hypervalent iodine-based chiral auxiliaries

“…16–19 In addition, a serious problem associated with transition-metal-promoted reaction is the product contamination, which is not observed with iodine( iii / v ) reagents. Therefore, hypervalent iodine compounds are potential rivals to transition metals in many organic reactions as covered in several excellent review articles, 20–30 book chapters, and books. 31–39…”

“…[16][17][18][19] In addition, a serious problem associated with transition-metal-promoted reaction is the product contamination, which is not observed with iodine(III/V) reagents. Therefore, hypervalent iodine compounds are potential rivals to transition metals in many organic reactions as covered in several excellent review articles, [20][21][22][23][24][25][26][27][28][29][30] book chapters, and books. [31][32][33][34][35][36][37][38][39] Traditionaly, hypervalent iodine reagents are employed as stoichiometric reagents but recent studies have revealed their use as versatile catalysts, as reviewed by Singh, Wirth, and coworkers.…”

Recent Advances in the Synthesis of 3,n-Fused Tricyclic Indole Skeletons via Palladium-Catalyzed Domino Reactions

“…After that, especially within the last ten years, a variety of protocols for synthesis of these molecules have been developed and refined by researchers. Moreover, the palladium catalyst was also used extensively in cross-coupling reactions, such as Buchwald-Hartwig, Suzuki-Miyaura, Heck, Sonogashira, Negishi, and Stille to synthesize a variety of useful compounds [ 17 , 18 ].…”