A General and Highly Efficient Method for the Construction of Aryl‐Substituted N‐Heteroarenes

Liu, Chun; Han, Na; Song, Xiaoxiao; Qiu, Jieshan

doi:10.1002/ejoc.201000962

Cited by 43 publications

(14 citation statements)

References 37 publications

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“…2-Phenyl-5-nitropyridine (5-NO 2 -Hppy) is synthesized according to the available literature [25]. Chloride-bridged dimer 1 is prepared by the reaction of 5-NO 2 -Hppy and iridium trichloride hydrate (IrCl 3 ·H 2 O) [26].…”

Section: Introductionmentioning

confidence: 99%

“…The present study elucidates the syntheses and characterization of a series of new iridium(III) cyclometalated complexes ([Ir(5-NO 2 -ppy) 2 Cl] 2 (1, 5-NO 2 -ppy = 2-phenyl-5-nitropyridyl), Ir(5-NO 2 -ppy) 2 (PPh 3 )Cl (2, PPh 3 = -triphenylphosphine), Ir(5-NO 2 -ppy) 2 (pic) (3, pic = picolinic acid)), in which the strongly electron-withdrawing nitro groups are introduced to the pyridyl rings of the ppy ligands. The electrochemical and photophysical properties of the complexes are also investigated.2-Phenyl-5-nitropyridine (5-NO 2 -Hppy) is synthesized according to the available literature [25]. Chloride-bridged dimer 1 is prepared by the reaction of 5-NO 2 -Hppy and iridium trichloride hydrate (IrCl 3 ·H 2 O) [26].…”

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confidence: 99%

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New 2-phenyl-5-nitropyridyl containing iridium(III) cyclometalated complexes: syntheses, structures, electrochemistry and photophysical properties

Shen

Wang

Sun

et al. 2011

Inorganic Chemistry Communications

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Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

New 2-phenyl-5-nitropyridyl containing iridium(III) cyclometalated complexes: syntheses, structures, electrochemistry and photophysical properties

Shen

Wang

Sun

et al. 2011

Inorganic Chemistry Communications

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“…TheR h À C Ph bond is selectively cleaved by one molar equivalent of HBF 4 to resultinthe formation of the rare agostic Synthesis of ligand 1 H :T his is am odified procedure. [27] tBuLi (1.6 m in pentane, 0.96 mL, 1.54 mmol, 1equiv) was added to as olution of 2-phenyl-6-methylpyridine [28] (0.26 g, 1.54 mmol) in THF (10 mL) cooled to À78 8C. The solution was stirred at À78 8Cf or 2h and P(tBu) 2 Cl (0.29 mL, 1.54 mmol) was added dropwise.…”

Section: Resultsmentioning

confidence: 99%

Facile Synthesis and Versatile Reactivity of an Unusual Cyclometalated Rhodium(I) Pincer Complex

Jongbloed

Bruin

Reek

et al. 2015

Chemistry A European J

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The synthesis of the reactive PN(C(H) ) ligand 2-di(tert-butylphosphanomethyl)-6-phenylpyridine (1(H) ) and its versatile coordination to a Rh(I) center is described. Facile C-H activation occurs in the presence of a (internal) base, thus resulting in the new cyclometalated complex [Rh(I) (CO)(κ(3) -P,N,C-1)] (3), which has been structurally characterized. The resulting tridentate ligand framework was experimentally and computationally shown to display dual-site proton-responsive reactivity, including reversible cyclometalation. This feature was probed by selective H/D exchange with [D1 ]formic acid. The addition of HBF4 to 3 leads to rapid net protonolysis of the Rh-C bond to produce [Rh(I) (CO)(κ(3) -P,N,(C-H)-1)] (4). This species features a rare aryl C-H agostic interaction in the solid state, as shown by X-ray diffraction studies. The nature of this interaction was also studied computationally. Reaction of 3 with methyl iodide results in rapid and selective ortho-methylation of the phenyl ring, thus generating [Rh(I) (CO)(κ(2) -P,N-1(Me) )] (5). Variable-temperature NMR spectroscopy indicates the involvement of a Rh(III) intermediate through formal oxidative addition to give trans-[Rh(III) (CH3 )(CO)(I)(κ(3) -P,N,C-1)] prior to C-C reductive elimination. The Rh(III) -trans-diiodide complex [Rh(I) (CO)(I)2 (κ(3) -P,N,C-1)] (6) has been structurally characterized as a model compound for this elusive intermediate.

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“…This was consistent with our reported results. [37][38][39] Hence, Pd(OAc) 2 is the best choice. Table 2, it is clear that the higher the temperature was, the better the result was obtained.…”

Section: Investigation Of Reaction Conditionsmentioning

confidence: 99%

Facile synthesis of mono-, bis- and tris-aryl-substituted aniline derivatives in aqueous DMF

Li¹,

Song²,

Ni³

et al. 2012

Arkivoc

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A facile, efficient and general protocol for synthesizing a series of mono-, bis-and tris-arylsubstituted aniline derivatives is described via the Pd(OAc) 2 -catalyzed aerobic and ligand-free Suzuki reaction of mono-, di-and tribromoanilines with aryl boronic acids in aqueous N,Ndimethylformamide (DMF). This is the first example to prepare 2,6-bisaryl-4-nitroanilines and 2,6-bisarylanilines via a palladium-catalyzed ligand-free Suzuki reaction.

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A General and Highly Efficient Method for the Construction of Aryl‐Substituted N‐Heteroarenes

Abstract: A general, simple and highly efficient method has been developed for the Pd(OAc) 2 -catalyzed ligand-free and aerobic

Cited by 43 publications

References 37 publications

New 2-phenyl-5-nitropyridyl containing iridium(III) cyclometalated complexes: syntheses, structures, electrochemistry and photophysical properties

New 2-phenyl-5-nitropyridyl containing iridium(III) cyclometalated complexes: syntheses, structures, electrochemistry and photophysical properties

Facile Synthesis and Versatile Reactivity of an Unusual Cyclometalated Rhodium(I) Pincer Complex

Facile synthesis of mono-, bis- and tris-aryl-substituted aniline derivatives in aqueous DMF

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