Hypervalent iodine reagents in the total synthesis of natural products

Silva, Luiz F.; Olofsson, Berit

doi:10.1039/c1np00028d

Cited by 282 publications

(31 citation statements)

References 438 publications

(634 reference statements)

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“…Hypervalent iodine compounds have emerged as selective and environmentally benign reagents in many areas of organic synthesis 1a,b. Diaryliodonium salts (Ar 2 IX), also named diaryl-λ 3 -iodanes, serve as versatile electrophilic arylating agents with a variety of carbon and heteroatom nucleophiles under both metal-free and metal-catalyzed conditions 2c…”

Section: Introductionmentioning

confidence: 99%

Arylation with Unsymmetrical Diaryliodonium Salts: A Chemoselectivity Study

Malmgren

Santoro

Jalalian

et al. 2013

Chemistry A European J

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238

163

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Phenols, anilines, and malonates have been arylated under metal-free conditions with twelve aryl(phenyl)iodonium salts in a systematic chemoselectivity study. A new “anti-ortho effect” has been identified in the arylation of malonates. Several “dummy groups” have been found that give complete chemoselectivity in the transfer of the phenyl moiety, irrespective of the nucleophile. An aryl exchange in the diaryliodonium salts has been observed under certain arylation conditions. DFT calculations have been performed to investigate the reaction mechanism and to elucidate the origins of the observed selectivities. These results are expected to facilitate the design of chiral diaryliodonium salts and the development of catalytic arylation reactions that are based on these sustainable and metal-free reagents.

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Section: Introductionmentioning

confidence: 99%

Arylation with Unsymmetrical Diaryliodonium Salts: A Chemoselectivity Study

Malmgren

Santoro

Jalalian

et al. 2013

Chemistry A European J

Self Cite

238

163

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“…Hypervalent iodine chemistry has become a focus of valuable research for designing robust methodologies in synthetic 1 and natural product chemistry. 2 Hypervalent iodine reagents are promising alternatives to the heavymetal oxidants due to their ready availability, easy handling, low toxicity and environmentally-benign nature. 3 Synthetic applications of these reagents have seen exponential growth as realised by several books, 4,5 chapters in books 6,7 and comprehensive reviews [8][9][10][11] published in this area.…”

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 this short review, we want to discuss recent advances in atom-economical transformations using hypervalent iodine reagents (iodanes) as electrophilic group-transfer reagents. Iodanes, in particular iodonium salts, are well-balanced reagents in terms of stability, reactivity and synthetic and/or commercial availability and therefore it is not surprising to see these compounds as key reagents in a great number of recently developed transformations [ 3 – 15 ]. However, in terms of atom economy, they have an intrinsic problem: their high reactivity is based on the emergence of aryl iodides as supernucleofuges.…”

Section: Introductionmentioning

confidence: 99%

Atom-economical group-transfer reactions with hypervalent iodine compounds

Boelke¹,

Finkbeiner²,

Nachtsheim³

2018

Beilstein J. Org. Chem.

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Hypervalent iodine compounds, in particular aryl-λ3-iodanes, have been used extensively as electrophilic group-transfer reagents. Even though these compounds are superior substrates in terms of reactivity and stability, their utilization is accompanied by stoichiometric amounts of an aryl iodide as waste. This highly nonpolar side product can be tedious to separate from the desired target molecules and significantly reduces the overall atom efficiency of these transformations. In this short review, we want to give a brief summary of recently developed methods, in which this arising former waste is used as an additional reagent in cascade transformations to generate multiple substituted products in one step and with high atom efficiency.

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Hypervalent iodine reagents in the total synthesis of natural products

Cited by 282 publications

References 438 publications

Arylation with Unsymmetrical Diaryliodonium Salts: A Chemoselectivity Study

Arylation with Unsymmetrical Diaryliodonium Salts: A Chemoselectivity Study

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

Atom-economical group-transfer reactions with hypervalent iodine compounds

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