Ruthenium/TFA-catalyzed regioselective C-3-alkylation of indoles with terminal alkynes in water: efficient and unprecedented access to 3-(1-methylalkyl)-1H-indoles

Cadierno, Victorio; Francos, Javier; Gimeno, José

doi:10.1039/c002804e

Cited by 34 publications

(17 citation statements)

References 29 publications

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“…Armstrong et al described a Sc(OTf) 3 ‐catalyzed nucleophilic substitution of indolylmethyl Meldrum's acids 11. Intermolecular hydroarylation of indoles with alkenes in the presence of [(PPh 3 )AuCl]/AgOTf12a and with alkynes in the presence of ruthenium complexes/TFA12b have also been demonstrated.…”

Section: Introductionmentioning

confidence: 99%

Fe(OTf)₃‐Catalyzed Aromatization of Substituted 3‐Methyleneindoline and Benzofuran Derivatives: A Selective Route to C‐3‐Alkylated Indoles and Benzofurans

et al. 2015

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A simple and convenient approach was developed to the selective synthesis of 3‐substituted indoles and benzofurans by the isomerization of 3‐methyleneindoline and benzofuran derivatives catalyzed by Fe(OTf)3. The salient features of this method are the easy availability of substrates, high yield, mild reaction conditions, tolerance of a variety of functional groups, and use of an environmentally friendly catalyst. A possible mechanism has also been proposed for the isomerization process.

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Section: Introductionmentioning

confidence: 99%

Fe(OTf)₃‐Catalyzed Aromatization of Substituted 3‐Methyleneindoline and Benzofuran Derivatives: A Selective Route to C‐3‐Alkylated Indoles and Benzofurans

et al. 2015

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“…3‐(1‐Methylheptyl)‐1 H ‐indole (5h): 5b Pale yellow oil. 1 H NMR (CDCl 3 ): δ = 0.83–0.90 (m, 3 H, ‐CH 2 ‐C H 3 ), 1.25–131 (m, 8 H, ‐C 4 H 8 ‐CH 3 ), 1.35 (d, J = 6.9 Hz, 3 H, CH‐CH 3 ), 1.58–1.62 (m, 1 H), 1.75–1.80 (m, 1 H), 3.05 (m, 1 H, CH 3 ‐C H ), 6.94 (s, 1 H, ‐NH‐C H =), 7.06–7.19 (m, 2 H, Ar), 7.36 (d, J = 6.9 Hz, 1 H, Ar), 7.66 (d, J = 3.8 Hz, 1 H), 7.86 (s, 1 H, ‐N H ‐) ppm.…”

Section: Methodsmentioning

confidence: 99%

Transition‐Metal‐Catalyzed Regioselective Alkylation of Indoles with Alcohols

Putra¹,

Takigawa²,

Tanaka³

et al. 2013

Eur J Org Chem

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The regioselective alkylation of indoles with alcohols as alkylating reagents was developed by using Pd/C or RuCl2(PPh3)3/DPEphos {DPEphos = bis[(2‐diphenylphosphanyl)phenyl] ether}as catalysts. The reaction of indole with benzyl alcohol in the presence of Pd/C and K2CO3 at 80 °C for 24 h without any solvent under in air yielded 90 % of 3‐benzylindole. The corresponding 3‐benzylindole was obtained in 99 % yield when the reaction was catalyzed by RuCl2(PPh3)3/DPEphos in the presence of K3PO4 at 165 °C for 24 h under argon. Several types of alcohols were treated with indoles under these conditions to give the corresponding 3‐alkylated indoles in high yields (up to 99 %). This reaction may involve the catalyst‐mediated transformation of alcohols to aldehydes, nucleophilic addition of indole to the resulting aldehydes accompanied by dehydration, and then hydrogenation.

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“…TFA is also important in the synthesis of amino acids [23] and deprotection of peptides [24]. As a strongly acidic catalyst, TFA has been extensively used in alkylation [25], acylation of aromatic compounds, and olefin polymerization. As far as we are aware TFA has not been used for synthesis of b-acetamido ketones.…”

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confidence: 99%

One-pot synthesis of β-acetamido-β-arylpropiophenone employing trifluoroacetic acid as an efficient catalyst

et al. 2011

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Trifluoroacetic acid as an efficient catalyst promoting the Dakin-West reaction at ambient temperature is reported for the first time in this paper. A few efficacious auxiliary catalysts were also developed for the Dakin-West reaction. A variety of substituted aryl aldehydes and aryl ketones were found to be applicable to the preparation of some new b-acetamido-b-arylpropiophenones. This procedure has several advantages such as high yields, short reaction time, and smaller amount (0.30 mol%) of catalyst.

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Ruthenium/TFA-catalyzed regioselective C-3-alkylation of indoles with terminal alkynes in water: efficient and unprecedented access to 3-(1-methylalkyl)-1H-indoles

Cited by 34 publications

References 29 publications

Fe(OTf)₃‐Catalyzed Aromatization of Substituted 3‐Methyleneindoline and Benzofuran Derivatives: A Selective Route to C‐3‐Alkylated Indoles and Benzofurans

Fe(OTf)₃‐Catalyzed Aromatization of Substituted 3‐Methyleneindoline and Benzofuran Derivatives: A Selective Route to C‐3‐Alkylated Indoles and Benzofurans

Transition‐Metal‐Catalyzed Regioselective Alkylation of Indoles with Alcohols

One-pot synthesis of β-acetamido-β-arylpropiophenone employing trifluoroacetic acid as an efficient catalyst

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Ruthenium/TFA-catalyzed regioselective C-3-alkylation of indoles with terminal alkynes in water: efficient and unprecedented access to 3-(1-methylalkyl)-1H-indoles

Cited by 34 publications

References 29 publications

Fe(OTf)3‐Catalyzed Aromatization of Substituted 3‐Methyleneindoline and Benzo­furan Derivatives: A Selective Route to C‐3‐Alkylated Indoles and Benzofurans

Fe(OTf)3‐Catalyzed Aromatization of Substituted 3‐Methyleneindoline and Benzo­furan Derivatives: A Selective Route to C‐3‐Alkylated Indoles and Benzofurans

Transition‐Metal‐Catalyzed Regioselective Alkylation of Indoles with Alcohols

One-pot synthesis of β-acetamido-β-arylpropiophenone employing trifluoroacetic acid as an efficient catalyst

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Fe(OTf)₃‐Catalyzed Aromatization of Substituted 3‐Methyleneindoline and Benzofuran Derivatives: A Selective Route to C‐3‐Alkylated Indoles and Benzofurans

Fe(OTf)₃‐Catalyzed Aromatization of Substituted 3‐Methyleneindoline and Benzofuran Derivatives: A Selective Route to C‐3‐Alkylated Indoles and Benzofurans