Metal‐Free <i>O</i>‐Arylation of Carboxylic Acid by Active Diaryliodonium(III) Intermediates Generated <i>in situ</i> from Iodosoarenes

Dohi, Toshifumi; Koseki, Daichi; Sumida, Kohei; Okada, Kana; Mizuno, Serina; Kato, Asami; Kita, Yasuyuki

doi:10.1002/adsc.201700843

Cited by 37 publications

(13 citation statements)

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“…It was revealed that the electronic effect of the aryl rings was dominant during the reaction of p-anisyl (pyridyl) triflate 31 with phenols 32; the phenol nucleophiles selectively coupled to the electrondeficient pyridyl group to yield pyridyl ether 33 in 65-88% yield. This chemoselectivity trend has been further applied by other researchers to transfer the electron-poor aryl group of unsymmetrical iodonium salts, and it was noted that the TMP group serves as an improved dummy ligand for aryl transfer processes from heteroaryl(TMP)iodonium salts (Seidl et al, 2016;Dohi et al, 2017). In 2020, Stuart et al reported a convenient method for phenol arylation using the in-situ-generated aryl(TMP)iodonium salts 34 (Gallagher et al, 2020) (Figure 2A, Equation b).…”

Section: Heteroaryliodonium Salts As Highly Reactive Pseudo-halidesmentioning

confidence: 90%

“…This Cu(I)-catalyzed synthesis of diaryl ethers using diaryliodonium salts is a complementary strategy to the previously mentioned metal-free arylation of phenols. The arylation of oxygen nucleophiles using heteroaryliodonium salts was not limited to the preparation of aryl(heteroaryl) ethers; as in the cases of other oxygen nucleophiles, it was demonstrated that benzoic acid was also arylated to produce quinolin-3-yl benzoate via the in-situ-generated iodonium salt bearing a 3quinolyl group (Dohi et al, 2017). Further, the chemistry of cyclic iodonium salts has recently experienced growing development (Chatterjee and Goswami, 2017).…”

Section: Heteroaryliodonium Salts As Highly Reactive Pseudo-halidesmentioning

confidence: 99%

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Heteroaryliodonium(III) Salts as Highly Reactive Electrophiles

2020

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In recent years, the chemistry of heteroaryliodonium(III) salts has undergone significant developments. Heteroaryliodonium(III) salts have been found to be useful synthetic tools for the transfer of heteroaryl groups under metal-catalyzed and metal-free conditions for the preparation of functionalized heteroarene-containing compounds. Synthetic transformations mediated by these heteroaryliodonium(III) salts are classified into two categories: (1) reactions utilizing the high reactivity of the hypervalent iodine(III) species, and (2) reactions based on unique and new reactivities not observed in other types of conventional diaryliodonium salts. The latter feature is of particular interest and so has been intensively investigated in recent decades. This mini-review therefore aims to summarize the recent synthetic applications of heteroaryliodonium(III) salts as highly reactive electrophiles.

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Section: Heteroaryliodonium Salts As Highly Reactive Pseudo-halidesmentioning

confidence: 90%

Section: Heteroaryliodonium Salts As Highly Reactive Pseudo-halidesmentioning

confidence: 99%

Heteroaryliodonium(III) Salts as Highly Reactive Electrophiles

2020

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“…As they said, this effect was attributed to counterion activation of diaryliodonium salts. Kita and Dong dependently reported the PhIO‐mediated C−O couplings (Scheme ).…”

Section: Acids As Nucleophiliesmentioning

confidence: 99%

Recent Advances of Cinnamic Acids in Organic Synthesis

et al. 2020

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The great success of cinnamic acids was rooted in their multiple functional groups. Herein, reactions triggered by the radical addition, electrophilic addition, Michael addition and reactions of acids were thoroughly discussed and summarized. Multi-component reactions, rearrange-ments, stereoselective synthesis, coupling, additions will be depicted in detail. This review focused on advances of cinnamic acids in the last decade (2010)(2011)(2012)(2013)(2014)(2015)(2016)(2017)(2018)(2019)(2020). We hope this review will be good for a better understanding of these reagents and future research. * , [7,8] acyl [9] and ketonic [10] radicals were reported. Toluene, [8a-c,9] boron reagents, [8d] aldehydes, [8e] acids, [9b,c] amides, [9d,12e-f] ketones, [10a-b] ethers, [11a-c] alcohols, [12a] epoxides, [12b] nitriles [12a] were able to function as radical precursors.Mao and co-workers [4] reported the decarboxylative methylation of cinnamic acids. The DTBP was employed not only as the oxidant, but also as the methyl source.C vinyl À CF 3 compounds (like Panomifene, and Cyhalothrin) were useful in medicinal chemistry. [5b] Hence, numerous efforts have been devoted to the preparation of these compounds. In this decade, several applications of air-stable Togni's reagent [5a-c,6a] or NaSO 2 CF 3 [5d-f,6b] for the direct C vinyl À CF 3 construction from cinnamic acids have been reported. These radical addition and decarboxylative methods usually required a metal-catalyst (Ir, [5a] Cu [5c,e,6b] ) (Scheme 3)Hu and co-workers [6a] presented a protocol for the construction of C sp2 À CF 2 SO 2 R bonds with a Togni-type reagent. The [a] L.Scheme 1. Classification by mechanism Scheme 2. Radical cascade.

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“…Recently, facile direct esterification of carboxylic acids, representing a largely untapped branch of ester bond formation, has received intense attention . Among the reactions, significant contributions by Olofsson, Zhang and others have established the cross coupling of carboxylic acids with diaryliodonium salts. Additionally, utilization of the copper catalysts in the oxidative coupling of carboxylic acids with boronic acids, known as the Chan‐Lam reaction, has provided an attractive way to access ester‐containing products (Scheme a) .…”

Section: Introductionmentioning

confidence: 99%

Enol Ester Intermediate Induced Metal‐Free Oxidative Coupling of Carboxylic Acids and Arylboronic Acids

Feng

2019

Eur J Org Chem

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A facile, efficient and environmentally friendly methodology for the preparation of phenolic esters is realized via metal‐free coupling of carboxylic acids and arylboronic acids. This sequential one pot reaction, employing methyl propiolate as an activating reagent, proceeds through the formation of enol ester intermediate, followed by a nucleophilic attack on the C‐O bond under the oxidation of hydrogen peroxide. These studies display that enol esters, despite previously being overlooked as synthetic intermediates, would be the valuable building blocks for developing carbon–carbon and carbon–heteroatom bond‐forming reactions.

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Metal‐Free O‐Arylation of Carboxylic Acid by Active Diaryliodonium(III) Intermediates Generated in situ from Iodosoarenes

Cited by 37 publications

References 70 publications

Heteroaryliodonium(III) Salts as Highly Reactive Electrophiles

Heteroaryliodonium(III) Salts as Highly Reactive Electrophiles

Recent Advances of Cinnamic Acids in Organic Synthesis

Enol Ester Intermediate Induced Metal‐Free Oxidative Coupling of Carboxylic Acids and Arylboronic Acids

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