Indium‐Catalyzed Hydroamination/Hydrosilylation of Terminal Alkynes and Aromatic Amines through a One‐Pot, Two‐Step Protocol

Sakai, Norio; Takahashi, Nobuaki; Ogiwara, Yohei

doi:10.1002/ejoc.201402544

Cited by 28 publications

(19 citation statements)

References 67 publications

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“…The crude material was purified by a column chromatography (silica gel 60 F 254 , 95/5 = hexane/EtOAc) to give the corresponding Knoevenagel product 3 or 9 (followed by recrystallization, if necessary). 6, 125.4, 128.8, 129.3, 130.6, 132.7, 142.8, 164.4, 167 52.4, 111.4, 118.8, 119.7, 131.7, 143.4, 151.8, 165.3, 168 for 8 h, with the exception that recrystallization from hexane was performed after column 6,52.7,125.1,127.0,127.5,128.0,128.9,130.0,131.5,139.8,142.4,143.4,164.5,167.2;IR (neat) 7, 125.9, 129.1, 130.5, 131.2, 136.7, 141.4, 164.2, 166.8 7,52.8,126.9,127.3,129.1,130.1,130.5,134.5,134.8,141.1,164.0,166.5;IR (neat) 20.8,52.5,52.7,122.8,126.06,126.09,127.6,128.8,131.4,137.7,149.0,164.1,166.3,168.8;IR (neat) …”

Section: Methodsmentioning

confidence: 99%

“…5 We have joined several other researchers in reporting the indium-catalyzed conversions of various carbonyl compounds with a variety of functional groups. 6 Based on these reports, we anticipated that the indium compound that shows unique activation of typical carbonyl compounds will effectively promote a Knoevenagel condensation with a weak carbonyl compound that includes a coordinating functional group. 7 Herein, we report a novel catalytic system composed of indium chloride and acetic anhydride that effectively 3 promotes the Knoevenagel condensation of aromatic/aliphatic/heteroaromatic aldehydes with a variety of activated methylene compounds leading to the preparation of substituted alkene derivatives.…”

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confidence: 99%

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Indium(III)-Catalyzed Knoevenagel Condensation of Aldehydes and Activated Methylenes Using Acetic Anhydride as a Promoter

et al. 2015

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The combination of a catalytic amount of InCl3 and acetic anhydride remarkably promotes the Knoevenagel condensation of a variety of aldehydes and activated methylene compounds. This catalytic system accommodates aromatic aldehydes containing a variety of electron-donating and -withdrawing groups, heteroaromatic aldehydes, conjugate aldehydes, and aliphatic aldehydes. Central to successfully driving the condensation series is the formation of a geminal diacetate intermediate, which was generated in situ from an aldehyde and an acid anhydride with the assistance of an indium catalyst.

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

Indium(III)-Catalyzed Knoevenagel Condensation of Aldehydes and Activated Methylenes Using Acetic Anhydride as a Promoter

et al. 2015

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“…The [24] 6 5 8 5 6 9 -72 (68-71) [24] (Continues) produced pink crystals were filtered and washed with 5 ml of perchloric acid. [27] 10 4 8 5 9 7 -100 (98-99) [28] 11 5 82 Liquid (liquid) [29] 12 5.5 85 84-86 (82-84) [30] 13 6 8 0 9 2 -95 (93-95) [31] 14 5 84 119-121 (120-121) [32] (Continues) [27] 10 4 8 5 9 7 -100 (98-99) [28] 11 5 82 Liquid (liquid) [29] 12 5.5 85 84-86 (82-84) [30] 13 6 8 0 9 2 -95 (93-95) [31] 14 5 84 119-121 (120-121) [32] (Continues) …”

Section: General Procedures For Preparation Of Ferric Perchloratementioning

confidence: 99%

Hofmann N‐alkylation of aniline derivatives with alcohols using ferric perchlorate immobilized on SiO₂ as a catalyst through Box–Behnken experimental design

Ghanimati

Abdoli‐Senejani

Isfahani

et al. 2018

Applied Organom Chemis

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Funding information Islamic Azad University-Arak BranchAn efficient method for the N-alkylation of poorly nucleophilic amines using ferric perchlorate immobilized on SiO 2 as a catalyst is described. Fe(ClO 4 ) 3 was prepared from mixing iron(III) hydroxide and perchloric acid and adsorbed on silica gel. The catalyst was characterized using various techniques. The supported ferric perchlorate (Fe(ClO 4 ) 3 /SiO 2 ) revealed high efficiency and selectivity for N-alkylation of aromatic amines with alcohols to provide alkylated amines. Various secondary amines were synthesized from primary amines and alcohols in good to excellent yields, with water as the only by-product. The optimization of the reaction conditions was investigated using the response surface method, and involving the Box-Behnken design matrix. The conditions for optimal reaction yield and time were: amount of catalyst = 0.34 mmol, temperature = 60°C and molar ratio of amine to alcohol = 1.2.The catalyst was recovered and reused for five cycles without a considerable decrease in catalytic activity. The stability of the recycled catalyst was investigated. The proposed method has numerous advantages including procedure simplicity, short reaction times, low cost, good to excellent yields, reusability of the catalyst and mild and environmentally benign conditions.

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“…80 With unsymmetrical alkynes, the hydroamination step is highly regioselective with the formation of Markovnikov-type enamines. Experimental data support a reaction mechanism involving an aniline nucleophilic attack at a In(III) π-alkyne complex to yield an enamine/imine product.…”

Section: One-pot Hydroamination/hydrosilylation Of Alkynes With Anilimentioning

confidence: 99%

Gallium and Indium Compounds in Homogeneous Catalysis

Dagorne

Fliedel

Frémont

2016

Encyclopedia of Inorganic and Bioinorganic Chemistry

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The present contribution highlights the most recent and representative developments on the use of Ga and In species in homogeneous catalysis. Recent studies of various ligand‐supported Ga(III) and In(III) compounds in cyclic esters polymerization catalysis for the production of biodegradable polyester materials are also included. Various organic transformations may now be catalyzed using Ga(III) and In(III) Lewis acids allowing access to a wide range of valuable organic molecules through diverse reaction sequences. The recent use of stable and robust N ‐heterocyclic carbene Ga(III) and In(III) compounds as strong π‐Lewis acid catalysts for various organic reactions is also discussed: such species are certainly promising for the future developments of Ga(III)‐ and In(III)‐mediated reactions. Although Lewis acid‐assisted reactions certainly dominate the field in Ga(III) and In(III) chemistry, discrete low‐valent In(I) species, presently emerging in catalysis, clearly display a distinct reactivity allowing their exploitation both as soft Lewis acids and alkyl‐/allyl‐/arylating agents.

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Indium‐Catalyzed Hydroamination/Hydrosilylation of Terminal Alkynes and Aromatic Amines through a One‐Pot, Two‐Step Protocol

Cited by 28 publications

References 67 publications

Indium(III)-Catalyzed Knoevenagel Condensation of Aldehydes and Activated Methylenes Using Acetic Anhydride as a Promoter

Indium(III)-Catalyzed Knoevenagel Condensation of Aldehydes and Activated Methylenes Using Acetic Anhydride as a Promoter

Hofmann N‐alkylation of aniline derivatives with alcohols using ferric perchlorate immobilized on SiO₂ as a catalyst through Box–Behnken experimental design

Gallium and Indium Compounds in Homogeneous Catalysis

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Indium‐Catalyzed Hydroamination/Hydrosilylation of Terminal Alkynes and Aromatic Amines through a One‐Pot, Two‐Step Protocol

Cited by 28 publications

References 67 publications

Indium(III)-Catalyzed Knoevenagel Condensation of Aldehydes and Activated Methylenes Using Acetic Anhydride as a Promoter

Indium(III)-Catalyzed Knoevenagel Condensation of Aldehydes and Activated Methylenes Using Acetic Anhydride as a Promoter

Hofmann N‐alkylation of aniline derivatives with alcohols using ferric perchlorate immobilized on SiO2 as a catalyst through Box–Behnken experimental design

Gallium and Indium Compounds in Homogeneous Catalysis

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Hofmann N‐alkylation of aniline derivatives with alcohols using ferric perchlorate immobilized on SiO₂ as a catalyst through Box–Behnken experimental design