Hypervalent Iodine Reagents in Palladium-Catalyzed Oxidative Cross-Coupling Reactions

Shetgaonkar, Samata E.; Singh, Fateh V.

doi:10.3389/fchem.2020.00705

Cited by 28 publications

(17 citation statements)

References 128 publications

(125 reference statements)

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“…Wengryniuk's group later published a piece of a review in 2017 that outlines the critical significance of polyvalent iodine reagents in high-valent palladium chemistry [37]. Polyvalent iodine compounds react efficiently with palladium complexes due to their electrophilic nature and oxidizing property, promoting reactions through Pd(0/II) and Pd(II/IV) catalytic cycles [38]. Furthermore, a handful of these se compounds are used as aryl, alkynyl, and heteroatom ligand sources in several Pd-catalyzed ligand transfer processes.…”

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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“…[2][3][4][5][6] Molecular oxygen, quinones, stoichiometric amounts of metal salts and hyper-valent iodine have all been deployed for the re-oxidation of Pd catalysts in oxidative reactions. [7][8][9][10][11][12] The application of molecular oxygen as a terminal oxidant for the catalyst (that is, to re-oxidize transition metals that have re-oxidized Pd) represents an especially powerful tool for organic transformation. [13] A practical example is the Wacker oxidation, which provides an aldehyde from ethylene and water.…”

Section: Introductionmentioning

confidence: 99%

Synergic Palladium Catalysis for Aerobic Oxidative Coupling

Tabaru

Obora

2022

Eur J Org Chem

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Aerobic oxidative coupling is a dehydrogenative organic transformation in which molecular oxygen acts as a re-oxidant for the catalyst system. Pd has emerged as one of the most popular transition metal catalysts for such reactions. Combinations of Pd with other transition metal catalysts can also provide effective catalytic cycles together with highly atom-and step-economical organic transformations. A synergic Pd catalyst system can promote such reactions with a high degree of efficiency based on a re-oxidation step exhibiting improved kinetics in which two electrons are transferred from another transition metal. This occurs in conjunction with a lower energy barrier than that associated with direct re-oxidation by molecular oxygen. This review highlights recent developments in aerobic oxidative coupling reactions catalyzed by synergic combinations of Pd with other transition metals. Highlighted reactions include dehydrogenative CÀ C bond formation such as arylation of arenes, heteroarenes, alkenes and dehydrogenative CÀ N and CÀ O bond formations with unsaturated hydrocarbons such as alkenes, 1,3-dienes and allenes. Moreover, mechanistic insights into these aerobic reactions based on experimental, computational and optical studies are detailed.

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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%

“…Hypervalent iodine reagents as oxidants facilitate the desired oxidation at the metal center and also provide heteroatom ligands such as acetate or chloride which are subsequently transferred to the substrates via reductive elimination. To date, palladium has been exclusively used as a catalyst in various oxidative coupling reactions involving the direct functionalization of C (sp 2 )-H and C (sp 3 )-H bonds (Deprez and Sanford, 2007;Silva et al, 2017;Shetgaonkar and Singh, 2020). On the other hand, other transition metals do catalyze such oxidative coupling reactions in the presence of hypervalent iodine 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 in Palladium-Catalyzed Oxidative Cross-Coupling Reactions

Cited by 28 publications

References 128 publications

Palladium-Catalyzed Organic Reactions Involving Hypervalent Iodine Reagents

Palladium-Catalyzed Organic Reactions Involving Hypervalent Iodine Reagents

Synergic Palladium Catalysis for Aerobic Oxidative Coupling

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

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