Hypervalent Iodine Reagents for Oxidative Rearrangements
28 Feb 2021-Mini-reviews in Organic Chemistry (Bentham Science Publishers Ltd.)-Vol. 18, Iss: 2, pp 138-158
TL;DR: In this mini-review, the recent developments in the area of oxidative rearrangements, using hypervalent iodine reagents, have been covered.
Abstract:
The chemistry of hypervalent iodine reagents has emerged as an astonishing field in
synthetic organic chemistry owing to its easy availability and benign environmental features.
Hypervalent iodine reagents are mostly employed as alternatives in various metal-catalyzed reactions
since they show similar reactivity to the transition metals, are less toxic, and less expensive. These
reagents are often used as oxidants as well as electrophilic reagents in a number of organic transformations,
such as oxidative functionalization, alpha C-H bond functionalization of carbonyl
compounds, rearrangements, and cyclization reactions. Furthermore, the application of iodine(III)
and iodine(V) reagents in various oxidative rearrangement processes generating a diverse array of
molecules have been well explored. In this mini-review, the recent developments in the area of
oxidative rearrangements, using hypervalent iodine reagents, have been covered.
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TL;DR: The aim of this review is to highlight recent developments in the utilisation of iodine(III) and iodine(V) catalysts in the synthesis of a wide range of organic compounds including chiral catalysts for stereoselective synthesis.
Abstract: Hypervalent iodine compounds as environmentally friendly and relatively inexpensive reagents have properties similar to transition metals. They are employed as alternatives to transition metal catalysts in organic synthesis as mild, nontoxic, selective and recyclable catalytic reagents. Formation of C-N, C-O, C-S, C-F and C-C bonds can be seamlessly accomplished by hypervalent iodine catalysed oxidative functionalisations. The aim of this review is to highlight recent developments in the utilisation of iodine(III) and iodine(V) catalysts in the synthesis of a wide range of organic compounds including chiral catalysts for stereoselective synthesis. Polymer-, magnetic nanoparticle- and metal organic framework-supported hypervalent iodine catalysts are also described.
23 citations
TL;DR: In this paper, two electronically different α-aryl-β,β-ditosyloxy ketones were successfully described by means of IR, 1H & 13C NMR, HRMS and crystal structure.
14 citations
TL;DR: The use 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 as discussed by the authors .
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.
7 citations
TL;DR: 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.
Abstract: Graphical Abstract 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.
5 citations
TL;DR: In this paper , the authors present a review of various aqueous mediated reactions involving hypervalent iodine reagents, including coupling reactions, cyclization reactions and halogenations reactions.
3 citations