Hypervalent iodine chemistry and light: photochemical reactions involving hypervalent iodine chemistry

Singh, Fateh V.; Wirth, Thomas

doi:10.24820/ark.5550190.p011.483

Cited by 23 publications

(23 citation statements)

References 89 publications

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“…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.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Organic Reactions Involving Hypervalent Iodine Reagents

et al. 2022

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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.

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Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Organic Reactions Involving Hypervalent Iodine Reagents

et al. 2022

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“…In addition to this, cyclic iodine(V) reagents, namely, Dess-Martin periodinane (DMP) 18 and 2-iodoxybenzoic acid (IBX) 19 are strong oxidizing agents (Uyanik and Ishihara, 2009). Several studies (Singh and Wirth, 2014a;Elsherbini and Wirth, 2018;Grelier et al, 2018;Hyatt et al, 2019;Shetgaonkar and Singh 2020;Shetgaonkar et al, 2021;Shetgaonkar et al, 2021;Singh and Wirth, 2021;Kumar et al, 2022) and books chapters (Singh and Wirth, 2014b;Singh and Wirth, 2017;Singh and Wirth, 2018) have been published covering the preparations and synthetic applications of these reagents.…”

Section: Introductionmentioning

confidence: 99%

Non-Palladium-Catalyzed Oxidative Coupling Reactions Using Hypervalent Iodine Reagents

et al. 2022

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Transition metal-catalyzed direct oxidative coupling reactions via C–H bond activation have emerged as a straightforward strategy for the construction of complex molecules in organic synthesis. The direct transformation of C–H bonds into carbon–carbon and carbon–heteroatom bonds renders the requirement of prefunctionalization of starting materials and, therefore, represents a more efficient alternative to the traditional cross-coupling reactions. The key to the unprecedented progress made in this area has been the identification of an appropriate oxidant that facilitates oxidation and provides heteroatom ligands at the metal center. In this context, hypervalent iodine compounds have evolved as mainstream reagents particularly because of their excellent oxidizing nature, high electrophilicity, and versatile reactivity. They are environmentally benign reagents, stable, non-toxic, and relatively cheaper than inorganic oxidants. For many years, palladium catalysis has dominated these oxidative coupling reactions, but eventually, other transition metal catalysts such as gold, copper, platinum, iron, etc. were found to be promising alternate catalysts for facilitating such reactions. This review article critically summarizes the recent developments in non-palladium-catalyzed oxidative coupling reactions mediated by hypervalent iodine (III) reagents with significant emphasis on understanding the mechanistic aspects in detail.

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“…Hypervalent iodine reagents have proven very useful for the synthesis of natural products and other bioactive compounds ( Dohi and Kita, 2016 ; Wang, 2021 ). A variety of methodologies have been developed, in many cases combining the hypervalent iodine reagents with other compounds, such as iodine, organic peroxides, TEMPO, and organic photosensitizers or metal catalysts in catalytic photoredox processes ( Singh and Wirth, 2021 ; Le Du et al, 2021 ; Zhdankin, 2020 ; Chen et al, 2020 ; Wang and Studer, 2017 ; Yoshimura and Zhdankin, 2016 ; Wang and Liu, 2016 ; Zhdankin and Stang, 2008 ; 2002 ).…”

Section: Introductionmentioning

confidence: 99%

“Cut and Paste” Processes in the Search of Bioactive Products: One-Pot, Metal-free O-Radical Scission-Oxidation-Addition of C, N or P-Nucleophiles

et al. 2022

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Hypervalent iodine reagents have been applied in many metal-free, efficient synthesis of natural products and other bioactive compounds. In particular, treatment of alcohols, acetals and acids with hypervalent iodine reagents and iodine results in O-radicals that can undergo a β-scission reaction. Under these oxidative conditions, derivatives of amino acids, peptides or carbohydrates are converted into cationic intermediates, which can subsequently undergo inter- or intramolecular addition of nucleophiles. Most reported papers describe the addition of oxygen nucleophiles, but this review is focused on the addition of carbon, nitrogen and phosphorous nucleophiles. The resulting products (nucleoside and alkaloid analogs, unnatural amino acids, site-selectively modified peptides) are valuable intermediates or analogs of bioactive compounds.

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Hypervalent iodine chemistry and light: photochemical reactions involving hypervalent iodine chemistry

Cited by 23 publications

References 89 publications

Palladium-Catalyzed Organic Reactions Involving Hypervalent Iodine Reagents

Palladium-Catalyzed Organic Reactions Involving Hypervalent Iodine Reagents

Non-Palladium-Catalyzed Oxidative Coupling Reactions Using Hypervalent Iodine Reagents

“Cut and Paste” Processes in the Search of Bioactive Products: One-Pot, Metal-free O-Radical Scission-Oxidation-Addition of C, N or P-Nucleophiles

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