Reactions promoted by hypervalent iodine reagents and boron Lewis acids

Abstract

Understanding the role of boranes in hypervalent iodine chemistry will open up new reactivities which can be utilised in organic synthesis. Due to similar reactivities, λ3-iodanes have presented themselves as...

C(sp3)–H Ritter amination by excitation of in situ generated iodine(iii)–BF3 complexes

“…Other acids or bases are not effective in this transformation due to the absence of strong interactions with the formed iodine( iii ) reagents. 10 The control experiments confirmed the essential roles of light and iodobenzene as an organocatalyst (entries 6 and 7). Also, the reaction from commercially available iodine( iii ) reagents as a combined precatalyst and terminal oxidant gave lower product yields (entries 8 and 9).…”

Palladium-Catalyzed Organic Reactions Involving Hypervalent Iodine Reagents

“…Various scientific papers, book chapters, and review articles have been published on the chemistry of hypervalent iodine. [10][11][12][13][14][15][16][17][18]. The functionalization of carbonyl compounds [19,20], cyclization [21][22][23][24], oxidative rearrangements [25][26][27], alkene difunctionalizations [28][29][30][31], and atom-transfer reactions [32], in the presence of hypervalent iodine compounds as reagents or catalysts, is now well established.…”

Aqueous Mediated Reactions Involving Hypervalent Iodine Reagents

“…Further, because of high electrophilic nature, hypervalent iodine reagents have been widely used to activate carbon‐carbon double bonds [46] . Moreover, in recent years, a number of coupling reactions leading to the formation of C−C, C−N and other carbon‐element bonds [47] and visible‐light photoredox catalysis [48] reactions have been carried out using these regents⋅ When incorporated with Lewis acids such as boranes, activation of these reagents is achieved [49] . Furthermore, development and utilization of numerous recyclable hypervalent iodine reagents have overcome the main drawback of stoichiometric hypervalent iodine reagents which produce non‐recyclable aryl iodides or co‐products after the completion of reaction [50] .…”

“…When incorporated with Lewis acids such as boranes, activation of these reagents is achieved. [49] Furthermore, development and utilization of numerous recyclable hypervalent iodine reagents have overcome the main drawback of stoichiometric hypervalent iodine reagents which produce non-recyclable aryl iodides or coproducts after the completion of reaction. [50] The facile formation of cationic intermediates has been used in various rearrangements for the formation of functionalized molecule, including oxidative ring expansions in aqueous media.…”