Metal-free C–H arylation of aminoheterocycles with arylhydrazines

Taniguchi, Tsuneo; Imoto, Mitsutaka; Takeda, Motonori; Matsumoto, Fukashi; Nakai, Tadashi; Mihara, Masahito; Mizuno, Takumi; Nomoto, Akihiro

doi:10.1016/j.tet.2016.05.056

Cited by 29 publications

(20 citation statements)

References 38 publications

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“…One is a photoinduced decomposition of triarylbismuthines and the other is an air‐induced decomposition of arylhydrazines . In the latter method, arylhydrazine hydrochlorides can be employed as an aryl radical source, and by using this method, we successfully developed the arylation of aminoheterocycles and aromatic diamines, the synthesis of unsymmetrical diaryl sulfides and selenides, and the aryl iodide synthesis by the trapping of aryl radicals with I 2 . On the basis of these studies, we have investigated the reaction of arylhydrazine hydrochlorides with diaryl ditellurides to synthesize symmetrical and unsymmetrical diaryl tellurides.…”

Section: Introductionmentioning

confidence: 99%

Reaction of arylhydrazines with diaryl ditellurides in the air: Insight into bimolecular homolytic substitution on tellurium via Aryl–Te bond cleavage

Yamamoto

Sato

Kodama

et al. 2018

Heteroatom Chemistry

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The reactivity of diaryl ditelluride and diaryl telluride toward aryl radicals was studied in detail. Diphenyl ditelluride underwent a bimolecular homolytic substitution (SH2) reaction with a phenyl radical generated from phenylhydrazine in the air, to afford diphenyl telluride in excellent yield. Based on this diphenyl telluride synthesis, a one‐pot synthesis of unsymmetrical diaryl tellurides was developed by the SH2 reaction of in situ generated diphenyl telluride with arylhydrazines in the air. The selectivity of mono‐/di‐substitution and the reactivity of arylhydrazines depend on the nature of the substituents on the arylhydrazines, that is, electron‐donating or ‐withdrawing group.

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Section: Introductionmentioning

confidence: 99%

Reaction of arylhydrazines with diaryl ditellurides in the air: Insight into bimolecular homolytic substitution on tellurium via Aryl–Te bond cleavage

Yamamoto

Sato

Kodama

et al. 2018

Heteroatom Chemistry

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“…The oxidation of catechol with ammonium peroxydisulfate (APS) in the presence of nitro-substituted arylhydrazines leads to black, solid, inseparable product mixtures. Their analytical investigation by HR-ESI-MS, FTIR-, 13 C-NMR-and ESR-spectroscopy showed that oligomers are built by CÀ C, CÀ O, and CÀ Nbond formation, in some cases by the loss of the hydrazine Natoms. These oligomers contain aryl-aryl, aryl-O-aryl and aryl-N=N structural elements, amongst them radical species and diaryl azo compounds as known in dye stuffs.…”

Section: Resultsmentioning

confidence: 99%

“…It is worth mentioning that investigations of the enzyme-catalyzed autoxidation of phenolic azo dyes showed that aryl radicals are formed being transferred into aryl hydroperoxides. [19] The ss 13 C-NMR of the product mixture 17 showed some similarities to that of 3 a. However the ratio of intensities of the signals in the range of 110-130 ppm compared with 140-160 ppm is reversed, i. e. more aromatic carbon atoms are present connected to N-or O-atoms.…”

Section: For C 12 H 8 N 3 O 4 )mentioning

confidence: 97%

“…Arylation of electron rich aromatic compounds by aryl hydrazines with the elimination of dinitrogen was observed in air-oxidation in DMSO/K 2 CO 3 . [13] Aryl radicals 10 may also be involved in the formation of triarylhydrazines 16.…”

Section: For C 12 H 8 N 3 O 4 )mentioning

confidence: 99%

“…Solid state13 C-NMR spectrum of product 3 a (bottom), catechol (middle) and 4-nitrophenylhydrazine (top).…”

mentioning

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New Insights into Catechol Oxidation – Application of Ammonium Peroxydisulfate in the Presence of Arylhydrazines

et al. 2020

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The oxidative polymerisation of catechols in the presence of amino groups is an important reaction leading to polymers or oligomers of great practical importance. We present here, the oxidative polymerisation in the presence of nitro-substituted aryl hydrazines using ammonium peroxydisulfate (APS) as oxidizing reagent in the presence of Tris-buffer. Mixtures of deeply coloured oligomers are formed and analysed by FTIR-, NMR-, ESR-spectroscopy and, in particular, by HR-ESI MS. The reaction occurred by CÀ C, CÀ O and CÀ N bond formation leading to aryl-aryl, aryl-O-aryl, aryl-N=N structural elements. In some cases, both N-atoms of the starting aryl hydrazine have been lost during reaction. Remarkably, diaryl azo compounds as structurally similar with azo dyes were also formed. Their reaction with APS was investigated. These results provide new insight into the oxidative depletion of azo dyes with APS in industrial waste water treatment.

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Transition Metal‐Free Iodosobenzene‐Promoted Direct Oxidative 3‐Arylation of Quinoxalin‐2(H)‐ones with Arylhydrazines

et al. 2017

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A transition metal‐free iodosobenzene‐promoted direct oxidative 3‐arylation of quinoxalin‐2(H)‐ones was developed using various arylhydrazines under air. The protocol affords a variety of 3‐arylquinoxalin‐2(H)‐one derivatives in moderate to good yields. This method provides a rapid access to biologically interesting benzo[g]quinoxalinones and pyrido[3,4‐b]pyrazinones. The present methodology features high functional group tolerance including base‐sensitive groups as well as allyl‐ and benzyl‐substituted quinoxalin‐2(H)‐ones under mild reaction conditions.magnified image

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Metal-free C–H arylation of aminoheterocycles with arylhydrazines

Cited by 29 publications

References 38 publications

Reaction of arylhydrazines with diaryl ditellurides in the air: Insight into bimolecular homolytic substitution on tellurium via Aryl–Te bond cleavage

Reaction of arylhydrazines with diaryl ditellurides in the air: Insight into bimolecular homolytic substitution on tellurium via Aryl–Te bond cleavage

New Insights into Catechol Oxidation – Application of Ammonium Peroxydisulfate in the Presence of Arylhydrazines

Transition Metal‐Free Iodosobenzene‐Promoted Direct Oxidative 3‐Arylation of Quinoxalin‐2(H)‐ones with Arylhydrazines

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