Dimerization of ethynylaniline to a quinoline derivative using a ruthenium/gold heterobimetallic catalyst

Shelton, Phillip; Hilliard, Casie R.; Swindling, Michael; McElwee‐White, Lisa

doi:10.3998/ark.5550190.0011.813

Cited by 10 publications

(8 citation statements)

References 27 publications

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“…By the use of heterobimetallic Ru/Au catalyst a different reaction mode could be observed for the cyclisation of alkynlanilines (Scheme 16). 28 Subjection of these substrates to gold(I) or gold(III) compounds usually delivers indole 26 as single products. 29 By using the heterobimetallic catalyst, the dimerization of ethynylaniline to the quinoline derivative 27.…”

Section: Dual Catalysis (A) Bimetallic Catalysismentioning

confidence: 99%

Heterocycles from gold catalysis

2011

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The article reviews the most important developments in the synthesis of heterocycles by gold catalysts for reactions directly involving the heteroatoms in the reacting groups. Reactions without direct participation of the hetero atoms, for example in substrates with the heteroatom in a tether between the reacting groups, are not included. In the last decade homogeneous gold catalysis has emerged from a handful of scattered publications to a hot topic, an area with now hundreds of publications per year. Among the many different products accessible by the new methods developed, heterocycles are probably the most important class of compounds with significant impact on the synthesis of agrochemicals and pharmaceuticals.

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Section: Dual Catalysis (A) Bimetallic Catalysismentioning

confidence: 99%

Heterocycles from gold catalysis

2011

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“…The complex [Cp*IrCl 2 ] 2 (Cp* = pentamethylcyclopentadienyl) catalyzed the cyclization of 2‐ethynylanilines to 2,2′‐biindoles . Conversely, the dimerization of 2‐ethynylanilines promoted by InBr 3 , heterodimetallic CpRu(PPh 3 )Cl(µ‐dppm)AuI [Cp = cyclopentadienyl, dppm = 1,1‐bis(diphenylphosphino)methane], or dinuclear Au 2 (BIPHEP)(NTf 2 ) 2 [BIPHEP = (biphenyl‐2,2′‐diyl)bis(diphenylphosphine), NTf 2 = bis(trifluoromethylsulfonyl)imide] catalysts led to multifunctional quinolines . 4‐Alkyl‐2,3‐disubstituted quinolines were obtained in good yields through reactions between 2‐alkynylanilines and activated ketones such as β‐keto esters promoted by p ‐toluenesulfonic acid .…”

Section: Introductionmentioning

confidence: 99%

“…InBr 3 , [12] heterodimetallic CpRu(PPh 3 )Cl(μ-dppm)AuI [Cp = cyclopentadienyl, dppm = 1,1-bis(diphenylphosphino)methane], [13] or dinuclear Au 2 (BIPHEP)(NTf 2 ) 2 [BIPHEP = (biphenyl-2,2′-diyl)bis(diphenylphosphine), NTf 2 = bis(trifluoromethylsulfonyl)imide] catalysts led to multifunctional quinolines. [14] 4-Alkyl-2,3-disubstituted quinolines were obtained in good yields through reactions between 2-alkynylanilines and activated ketones such as -keto esters promoted by p-toluenesulfonic acid.…”

Section: Introductionmentioning

confidence: 99%

“…H NMR (400 MHz, CDCl 3 ): δ = 8.07 (dd, J = 9.2, J = 0.9 Hz, 1 H), 7.77 (dd, J = 1.6, J = 0.9 Hz, 1 H), 7.25 (dd, J = 9.2, J = 1.6 Hz, 1 H), 3.90 (br. s, 1 H, OH), 2.31 (td, J = 14.6, J = 7.4 Hz, 1 H, CH 2 ), 2.05 (td, J = 14.6, J = 7.6 Hz, 1 H, CH 2 ), 1.71 (s, 3 H, CH 3 ), 0.85 (t, J = 7.5 Hz, 3 H, CH 3 ) ppm 13. C NMR (100.6 MHz, CDCl 3 ): δ = 193.7 (C=O), 157.9 (C q ), 157.3 (C q ), 138.2 (C q ), 131.2 (CH), 122.7 (CH), 120.3 (C q ), 114.6 (CH), 79.4 (C q ), 32.4 (CH 2 ), 25.2 (CH 3 ), 7.8 (CH 3 ) ppm.…”

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confidence: 99%

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Sequential Silver‐Catalyzed Oxidative Cyclization Reactions of Unprotected 2‐Alkynylanilines to Anthranils

et al. 2017

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The full details of the original Ag-catalyzed domino oxidative cyclization reactions of unprotected 2-alkynylanilines with Oxone are described. The influences of several parameters including the substrate features, oxidant, reaction conditions, and catalyst on the reaction outcome were explored. A plausible mechanism is provided for the unusual silver-catalyzed oxidative cyclization reactions of 2-alkynylanilines to anthranils

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“…In addition, these limited literature methods are only viable to terminal alkynes. In those cases, the more sterically handed and less reactive internal alkynes chose to undergo intramolecular cyclization to give indoles rather than dimerization . To develop this intriguing reaction into a general and efficient synthesis of 2-(2-aminophenyl)quinolines from internal alkynes, several parameters possibly affecting its efficiency were screened.…”

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confidence: 99%

Selective Synthesis of 2-Indolyl-3-oxoindolines or 2-(2-Aminophenyl)quinolines through Cu(II)- or Bi(III)-Catalyzed Tunable Dimerizations of 2-Alkynylanilines

Jia

Zhang

et al. 2020

Org. Lett.

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A novel and selective synthesis of 2-indolyl-3oxoindolines or 2-(2-aminophenyl)quinolines through tunable dimerizations of 2-alkynylanilines is presented. Mechanistically, the formation of 2-indolyl-3-oxoindolines involves a Cu(OAc) 2 / O 2 -promoted intramolecular cyclization of 2-alkynylaniline to give the required indole and 3H-indol-3-one intermediates followed by the indolylation of 3H-indol-3-one. On the other hand, the formation of 2-(2-aminophenyl)quinolines is believed to go through a Bi(OTf) 3 /MesCO 2 H-catalyzed intermolecular N-nucleophilic addition between two 2-alkynylaniline molecules to give an enamine intermediate followed by its intramolecular C-nucleophilic addition/annulation. Notable features of these new methods include easily obtainable substrates, economical catalysts and oxidant, controllable selectivity, and high versatility toward diverse products.2,2-Disubstituted indolin-3-one constitutes the scaffold of numerous natural products such as Austamdine, Cephalinone, LipidGreen, Aristotelon, Isatisine A, and Halichrome A, 1 fluorescence probes, and solar-cell materials. 2 Among different kinds of 2,2-disubstituted indolin-3-one derivatives, 2-indolyl-3-oxoindolines are particularly attractive. This is because they not only have unique structural features but also demonstrate potent antiviral activities. 3 To date, several reliable methods for the preparation of 2-indolyl-3-oxoindolines have been reported by Ramana, Guchhait, Jiang, Liu, and many others. 4−6 In the past several years, we have developed some methods for the synthesis of biologically interesting heterocyclic compounds. 7 In this regard, we recently disclosed the synthesis of indolo[3,2-c]quinolines and 3-(2-aminophenyl)quinolines via [RhCp*Cl 2 ] 2 -catalyzed dimerization of 2-alkynylanilines under aerobic/anaerobic conditions (Schemes 1a and 1b). 7d In

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Dimerization of ethynylaniline to a quinoline derivative using a ruthenium/gold heterobimetallic catalyst

Cited by 10 publications

References 27 publications

Heterocycles from gold catalysis

Heterocycles from gold catalysis

Sequential Silver‐Catalyzed Oxidative Cyclization Reactions of Unprotected 2‐Alkynylanilines to Anthranils

Selective Synthesis of 2-Indolyl-3-oxoindolines or 2-(2-Aminophenyl)quinolines through Cu(II)- or Bi(III)-Catalyzed Tunable Dimerizations of 2-Alkynylanilines

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