Efficient oxidative biaryl coupling reaction of phenol ether derivatives using hypervalent iodine(III) reagents

Tohma, Hirofumi; Morioka, Hironori; Takizawa, Shinobu; Arisawa, Mitsuhiro; Kita, Yasuyuki

doi:10.1016/s0040-4020(00)00941-8

Cited by 183 publications

(71 citation statements)

References 76 publications

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“…A range of arenes worked comparably well under our reaction conditions to give the corresponding biaryls in moderate to good yields (Table 5). Even difficult substrates such as 4-nitroanisole, which was reported to be unreactive in Lewis acid mediated oxidative coupling [35], produced the corresponding biaryl in moderate yield (Table 5, entry 12). Highly electron deficient substrates like 1,3-dicholorobenzene also reacted at elevated temperature (Table 5, entry 16).…”

Section: Introductionmentioning

confidence: 99%

Gold-catalyzed direct oxidative coupling reactions of non-activated arenes

Kar

Mangu

Kaiser

et al. 2009

Journal of Organometallic Chemistry

102

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Section: Introductionmentioning

confidence: 99%

Gold-catalyzed direct oxidative coupling reactions of non-activated arenes

Kar

Mangu

Kaiser

et al. 2009

Journal of Organometallic Chemistry

102

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“…[41][42][43][44][45][46][47][48][49][50][51][52][53][54][55][56][57][58][59] Therefore, various types of recyclable hypervalent iodine reagents have been reported. First, the polymer-supported hypervalent iodine reagents, such as poly(diacetoxyiodo) styrene (PDAIS) and poly[bis(trifluoroacetoxyiodo)] styrene (PBTIS), incorporating phenyliodine(III) diacetate (PIDA) and phenyliodine(III) bis(trifluoroacetate) (PIFA) in their polymer backbones were developed.…”

Section: Resultsmentioning

confidence: 99%

“…First, the polymer-supported hypervalent iodine reagents, such as poly(diacetoxyiodo) styrene (PDAIS) and poly[bis(trifluoroacetoxyiodo)] styrene (PBTIS), incorporating phenyliodine(III) diacetate (PIDA) and phenyliodine(III) bis(trifluoroacetate) (PIFA) in their polymer backbones were developed. [41][42][43][44][45][46][47][48] Inspired by this study, other chemists have also reported new recyclable hypervalent iodine compounds having fluorous tags [49][50][51][52] and ionic supports. [53][54][55] We have previously developed a structurally new recyclable hypervalent iodine reagent 1a, namely, 1,3,5,7-tetrakis[4-(diacetoxyiodo) phenyl] adamantane ( Fig.…”

Section: Resultsmentioning

confidence: 99%

Clean Synthesis of <i>N</i>-Pyrrolyl Azoles by Metal-Free Oxidative Cross-Coupling Using Recyclable Hypervalent Iodine Reagent

Ogawa

Koseki

Takahashi

et al. 2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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The facile and clean oxidative coupling reaction of pyrroles with azoles has been achieved using the recyclable hypervalent iodine(III) reagents having adamantane structures. These iodine(III) reagents could be recovered from the reaction mixtures by a simple solid-liquid separation, i.e., filtration, for reuse.Key words oxidative coupling; hypervalent iodine reagent; recycle; pyrrole; azole; C-N bond formationThe N-pyrrolyl azoles are important fragments in the molecules of biological systems or in many pharmaceuticals, insecticides, and functional materials, especially, fluorescent dyes. [1][2][3][4] In spite of this interest, the preparations of N-aryl azoles are severely restricted because the nitrogen heteroaromatics are sometimes not a good substrate to use in the traditional arylation methods such as the Ullmann coupling, [5][6][7][8][9][10][11] since the pyrrole-based metal and halide compounds are sometimes unstable. Katritzky et al. reported the synthesis of pyrrolyl-benzotriazoles by the Mannich condensation of o-phthalaldehyde and 2,5-dimethoxy-2,5-dihydrofuran with primary amines, 12) but this method was not effective for pyrroles, and the desired products were produced only in less than 10% yields. As a new approach, the oxidative C-H bond functionalization strategies of pyrroles [13][14][15][16][17][18][19][20][21][22] might be expected to be an attractive methodology for enabling rapid access to these molecules. Recently, we have developed a new hypervalent iodine-induced oxidative coupling of pyrroles at the N 1 -positions of the azoles. 23) In 2014, Chen and colleagues reported the oxidative coupling method of 1,2,3-triazoles with pyrroles using N-iodosuccinimide (NIS) as an oxidant, in which the reactions preferentially occurred at the N 2 -position of the 1,2,3-triazoles.24) However, these methods produced stoichiometric quantities of iodoarene or succinimide as a waste product after the reaction (Chart 1).Hypervalent iodine reagents have received much attention due to their mild oxidation abilities and low toxicity, easy handling, as alternatives to toxic heavy metal reagents. [25][26][27][28][29][30][31][32] For developing a new coupling for heteroaromatic compounds, we have been engaged in the study of the oxidative C-H bond arylations using hypervalent iodine reagents that utilize the new reactivities of the heteroaromatic iodonium intermediates. [33][34][35][36][37] As mentioned, we developed a hypervalent iodineinduced oxidative coupling of pyrroles at the N 1 -positions of the azoles.23) This new method is versatile in allowing the reactions under metal-free and mild conditions, and tolerates a diverse series of functionalities of the pyrroles and azole coupling partners. We envisioned that a recycling version of this oxidative coupling should become feasible and provide an eco-friendly synthetic method (Chart 2) because a number of recent studies have demonstrated the utility of the recyclable hypervalent iodine reagents. 38-40) Results and DiscussionThe use of recyclable hypervalent ...

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“…The hypervalent iodine(III) reagent, PIFA, induced biaryl coupling reaction involving aromatic cation-radical intermediates was originally developed by our group 89,94,95,97) and applied to the synthesis of some useful heterocycles by Moreno et al 109) The commonly used conditions for biaryl coupling reactions using PIFA are as follows: (i) in poorly nucleophilic solvents such as TFE or HFIP; and (ii) in the presence of BF 3 ·Et 2 O (2 eq) in CH 2 Cl 2 .…”

Section: Oxidative Non-phenolic Coupling Reaction Leading To Biarylsmentioning

confidence: 99%

Development and Application of New Oxidation Systems Utilizing Oxometalate Catalysts

Hamamoto

2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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This review describes our recent efforts in the development and application of new oxidation systems utilizing oxometalate catalysts. The novel use of heteropoly acid (HPA), an acidic oxometalate catalyst, in hypervalent iodine-mediated oxidations provided an effective strategy to generate cation radical species that enables a variety of direct C-H functionalizations of aromatic compounds. This strategy brought a facile biaryl synthesis and new spirodienone syntheses in aromatic oxidation chemistry. Moreover, this strategy opens up a facile synthetic route to morphinandienone alkaloids. On the other hand, the use of oxometalate catalyst together with poly(N-isopropylacrylamide) (PNIPAAm)-based polymer in the development of new solid-phase catalyst provided a novel reaction system in water. Due to the characteristic temperature-responsive intelligence of PNIPAAm, this reaction system brought a remarkable acceleration of the reactivity and ease of catalyst recovering in catalytic oxidation that uses hydrogen peroxide or oxygen gas (O 2 ) as primary oxidant. In addition, the recovered solid-phase catalyst could be used for consecutive reactions without any significant loss of its catalytic efficacy.

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Efficient oxidative biaryl coupling reaction of phenol ether derivatives using hypervalent iodine(III) reagents

Cited by 183 publications

References 76 publications

Gold-catalyzed direct oxidative coupling reactions of non-activated arenes

Gold-catalyzed direct oxidative coupling reactions of non-activated arenes

Clean Synthesis of <i>N</i>-Pyrrolyl Azoles by Metal-Free Oxidative Cross-Coupling Using Recyclable Hypervalent Iodine Reagent

Development and Application of New Oxidation Systems Utilizing Oxometalate Catalysts

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