Synthesis of Dimethyl 2‐Phenylcyclopropane‐1,1‐Dicarboxylate Using an Iodonium Ylide Derived from Dimethyl Malonate

Goudreau, Sébastien R.; Marcoux, David; Charette, André B.

doi:10.1002/0471264229.os087.13

Cited by 9 publications

(4 citation statements)

References 23 publications

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“…Most iodonium ylides should be handled at low temperature or generated and used in situ because of the low thermal stability. The most practically important ylides, phenyliodonium bis(sulfonyl)methides, PhIC(SO 2 R) 2 , − and bis(carbonyl)methides, PhIC(COR) 2 , ,− are synthesized by treatment of (diacetoxyiodo)benzene with dicarbonyl compounds or disulfones in the presence of base. Ochiai and co-workers have developed a new procedure for the preparation of iodonium ylides by the transylidation reaction of halonium ylides under thermal conditions or under rhodium(II)-catalyzed conditions .…”

Section: Synthetic Applications Of Trivalent Iodine Compoundsmentioning

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: Synthetic Applications Of Trivalent Iodine Compoundsmentioning

confidence: 99%

Advances in Synthetic Applications of Hypervalent Iodine Compounds

2016

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“…83 An optimized method for preparing bis(methoxycarbonyl)(phenyliodonium)methanide (52, R 1 = R 2 = Me) using a similar reaction of dimethyl malonate ester with PhI(OAc) 2 and KOH in acetonitrile solution was published in Organic Syntheses in 2010. 89 Ylides 52 decompose slowly at room temperature but they can be kept for several weeks in a refrigerator.…”

Section: Preparation and Properties Of Iodonium Ylidesmentioning

confidence: 99%

Applications of iodonium salts and iodonium ylides as precursors for nucleophilic fluorination in Positron Emission Tomography

Yusubov¹,

Svitich²,

Ларькина³

et al. 2013

Arkivoc

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This review summarizes the applications of iodonium compounds in the rapidly developing field of Positron Emission Tomography (PET). Reactions of diaryliodonium salts with fluoride anion have found wide practical application in PET as a fast and convenient method for the introduction of the radioactive [18 F]-fluoride into radiotracer molecules. The best synthetic methods for the preparation of iodonium precursors for PET are described, the mechanistic aspects of nucleophilic fluorination reaction are discussed, and specific examples of the preparation of PET radioligands are provided.

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“…In the wake of great developments in hypervalent iodine chemistry, iodonium ylides have emerged as safe carbene precursors compared to diazo compounds . Nevertheless, the application of iodonium ylides as carbene precursors is also limited because of their low solubility in most solvents, difficulty of purification, and instability . Zhdankin and co-workers improved the solubility of aryliodonium ylides by introducing an alkoxy group in the ortho position of the phenyl group, extending the application of iodonium ylides. , However, the one-pot procedure, using iodonium-generated ylides in situ, is a more straightforward and effective process to overcome the shortcomings of iodonium ylides, because the procedure avoids isolation of the potentially unstable and low-solubility intermediates.…”

Section: Introductionmentioning

confidence: 99%

In Situ-Generated Iodonium Ylides as Safe Carbene Precursors for the Chemoselective Intramolecular Buchner Reaction

2014

J. Org. Chem.

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A chemoselective intramolecular Buchner reaction employing iodonium ylides as safe carbene precursors has been developed. Iodonium ylides are generated in situ from N-benzyl-2-cyanoacetamides and PhI(OAc)2 in the presence of base and undergo intramolecular Buchner reaction under catalysis from Cu(OAc)2·H2O, affording fused cyclohepta-1,3,5-triene derivatives in up to 85% yield. The N,N-dibenzyl-2-cyanoacetamides with two different benzyl groups undergo intramolecular Buchner reaction on their electron-rich benzyl groups selectively. The reaction is not sensitive to air and moisture and uses a safe alternative version of the corresponding diazo starting materials. The overall transformation involving the carbene pathway has been verified.

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Synthesis of Dimethyl 2‐Phenylcyclopropane‐1,1‐Dicarboxylate Using an Iodonium Ylide Derived from Dimethyl Malonate

Abstract: Potassium hydroxide Dimethyl malonate Iodosobenzene diacetate Bis[rhodium(a,a,a′a′‐tetramethyl‐1,3‐benznedipropionic acid)] Styrene Thiourea

Cited by 9 publications

References 23 publications

Advances in Synthetic Applications of Hypervalent Iodine Compounds

Advances in Synthetic Applications of Hypervalent Iodine Compounds

Applications of iodonium salts and iodonium ylides as precursors for nucleophilic fluorination in Positron Emission Tomography

In Situ-Generated Iodonium Ylides as Safe Carbene Precursors for the Chemoselective Intramolecular Buchner Reaction

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