α-Functionalization of Carbonyl Compounds Using Hypervalent Iodine Reagents

Merritt, Eleanor A.; Olofsson, Berit

doi:10.1055/s-0030-1258328

Cited by 68 publications

(6 citation statements)

References 109 publications

(132 reference statements)

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“…While chemical reactions catalyzed by iodine species have been discovered only in 2005, the electrochemical generation of iodine(III) species in situ from catalytic amounts of iodoarenes and the use of these species as the in-cell mediators in electrochemical fluorination reactions have been reported by Fuchigami and co-workers much earlier, in 1994 . The hypervalent iodine-catalyzed reactions have been discussed in several recent review articles. ,,− ,− ,− …”

Section: Iodine Compounds As Organocatalystsmentioning

confidence: 99%

Advances in Synthetic Applications of Hypervalent Iodine Compounds

2016

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The preparation, structure, and chemistry of hypervalent iodine compounds are reviewed with emphasis on their synthetic application. Compounds of iodine possess reactivity similar to that of transition metals, but have the advantage of environmental sustainability and efficient utilization of natural resources. These compounds are widely used in organic synthesis as selective oxidants and environmentally friendly reagents. Synthetic uses of hypervalent iodine reagents in halogenation reactions, various oxidations, rearrangements, aminations, C−C bond-forming reactions, and transition metal-catalyzed reactions are summarized and discussed. Recent discovery of hypervalent catalytic systems and recyclable reagents, and the development of new enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important achievement in the field of hypervalent iodine chemistry. One of the goals of this Review is to attract the attention of the scientific community as to the benefits of using hypervalent iodine compounds as an environmentally sustainable alternative to heavy metals.

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Section: Iodine Compounds As Organocatalystsmentioning

confidence: 99%

Advances in Synthetic Applications of Hypervalent Iodine Compounds

2016

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“…present in the amino acid side chain were well tolerated. Additionally, synthesis of terminal 15 N2diazirines was achieved from unlabelled amino acids using 15 NH3 as a nitrogen source. Finally, hyperpolarization of 15 N2-diazirine derivative was investigated using the SABRE-SHEATH method, demonstrating its potential application as hyperpolarized molecular tag.…”

Section: Synthesis Of Monocyclic Heterocyclesmentioning

confidence: 99%

“…Both iodine(III) and iodine(V) compounds (also known as λ 3 -iodane and λ 5 -iodane) have been commonly used as reagents in the oxidative transformations of various simple and complex organic molecules. [12][13][14] Most importantly, the unique reactivity and oxidizing ability of λ 3 -and λ 5 -iodanes has prompted their use as efficient oxidants in variety of synthetic transformations including α-functionalization of carbonyl compounds, 15,16 oxidative rearrangements, 17,18 alkene defunctionalization 19,20 and cyclization reactions. 21,22 However, most of this transformation requires stoichiometric amounts of these reagents, generating the same molar quantity of iodoarenes as by-product thus limiting their scope.…”

Section: Introductionmentioning

confidence: 99%

Hypervalent iodine-mediated synthesis and late-stage functionalization of heterocycles

Shetgaonkar¹,

Singh²

2021

Arkivoc

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Hypervalent iodine chemistry has witnessed exponential growth in organic synthesis in recent times. Because of the electrophilic and good-leaving nature of hypervalent iodine reagents, they react with different nucleophiles in various synthetic transformations such as rearrangements, α-functionalization of carbonyl compounds, alkene difunctionalization and oxidation reactions. Importantly, the application of hypervalent iodine reagents in the construction of heterocycles is of great interest and has been well studied over the years. This review article highlights the recent developments accomplished by hypervalent iodine reagents in the synthesis and functionalization of heterocyclic compounds.

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“…In spite of the considerable breakthroughs in recent α-alkylation of carbonyl derivatives, this field still requires significant improvements, such as increasing selectivity for branched or linear allylation, use of cheap metal catalysts for stereo-controlled alkylations, and environment-friendly reaction conditions. Several metal-free α-alkylation of carbonyl derivatives were investigated with this context [56], and a transient directing group (TDG) strategy could be considered for expanding the substrate scopes to relative unstable functionalities [57,58]. Especially, advances in stereo-controlled reactions of imines may expand synthetic utilities toward synthesis of biologically active amine-containing products with combinations of well-known diastereo-selective reactions.…”

Section: Conclusion and Outlooksmentioning

confidence: 99%

Transition Metal-Catalyzed α-Position Carbon–Carbon Bond Formations of Carbonyl Derivatives

et al. 2020

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α-Functionalization of carbonyl compounds in organic synthesis has traditionally been accomplished via classical enolate chemistry. As α-functionalized carbonyl moieties are ubiquitous in biologically and pharmaceutically valuable molecules, catalytic α-alkylations have been extensively studied, yielding a plethora of practical and efficient methodologies. Moreover, stereoselective carbon–carbon bond formation at the α-position of achiral carbonyl compounds has been achieved by using various transition metal–chiral ligand complexes. This review describes recent advances—in the last 20 years and especially focusing on the last 10 years—in transition metal-catalyzed α-alkylations of carbonyl compounds, such as aldehydes, ketones, imines, esters, and amides and in efficient carbon–carbon bond formations. Active catalytic species and ligand design are discussed, and mechanistic insights are presented. In addition, recently developed photo-redox catalytic systems for α-alkylations are described as a versatile synthetic tool for the synthesis of chiral carbonyl-bearing molecules.

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α-Functionalization of Carbonyl Compounds Using Hypervalent Iodine Reagents

Cited by 68 publications

References 109 publications

Advances in Synthetic Applications of Hypervalent Iodine Compounds

Advances in Synthetic Applications of Hypervalent Iodine Compounds

Hypervalent iodine-mediated synthesis and late-stage functionalization of heterocycles

Transition Metal-Catalyzed α-Position Carbon–Carbon Bond Formations of Carbonyl Derivatives

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