313663-95-5

Upstream product

• 120-72-9 indole 
• 930-30-3 cyclopent-2-enone 
• 133-32-4 4-indol-3-yl-butyric acid 
• 313663-93-3 1-diazo-5-(3-indolyl)-2-pentanone 

Relevant academic research and scientific papers

Alkylation of N-protecting group-free indole with vinyl ketones using iron salt catalyst

Indole was reacted with vinyl ketones in the presence of 3 mol % of iron(II) tetrafluoroborate in acetonitrile or ionic liquids to give 3-alkylated product in an excellent yield. 2,3-Dialkylated indole was also obtained when the reaction was carried out u

Supported iron catalysts for Michael addition reactions

Heterogeneous catalysts have been widely used for chemical transformations and offer easy product separation in addition to their high activity. Iron is an earth-abundant metal, but it has not been studied thoroughly as heterogeneous catalysts for organic

Development of solvent-driven iron-catalyzed reactions

The possibility of solvent-driven iron-catalyzed reactions has been investigated using ionic liquids and acetonitrile as key solvents. Three iron-catalyzed reactions, the intramolecular cyclization of cyclopropane dithioacetals, the [2+2]-cycloaddition of (trans)-anethole, and the [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone, were first developed using acetonitrile as solvent in the presence of 3～5 mol% of Fe(ClO4 )3 ?Al2 O3 or Fe(BF4 )2 ?6H2 O under air conditions. In particular, we found the rapid cycloaddition of iron-catalyzed [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone when the reaction was carried out in an ionic liquid which contained [PF6 ] or [Tf2N] anion. Homo-coupling reaction of aryl or alkynyl Grignard reagent was next discovered using 1 mol% of FeCl3 as catalyst and the reaction also proceeded very rapidly in an ionic liquid. We also found that 3～5 mol% of Fe(ClO4 )2 ?Al2 O3 or Fe(BF4 )2 ?6H2 O-successfully catalyzed Friedel-Crafts type alkylation of indoles or pyrroles with vinyl ketones or α-aryl-β-silylalcohol. In particular, the reaction of chiral α-aryl-β-silylalcohol with indole using Fe(ClO4 )3 ?nH2 O as catalyst proceeded with retention of the configuration of stereochemistry of the hydroxyl group. Then, we discovered the first example of iron-catalyzed enantioselective C-S bond formation via Michael addition of thiols to (E)-3-crotonoyloxazolidin-2-one using 10 mol% of Fe(BF4 )2 /Pybox. We further demonstrated that Fe(ClO4 )3 ?Al2 O3 -catalyzed the Nazarov type cyclizations of thiophene, pyrrole, indole, benzofuran, and benzo[b]thiophene derivatives using ionic liquids as solvent. Solvents have been recognized as a by-player in chemical reactions in the process of "optimization of reaction conditions". However, further investigation of the solvent-driven iron-catalyzed reaction will allow discovery of useful reactions for organic syntheses.

Strong Lewis acids of air-stable binuclear triphenylantimony(V) complexes and their catalytic application in C-C bond-forming reactions

Two air-stable novel Lewis acids of triphenylantimony(V) pentafluorbezenesulfonates (2) and perfluorooctanesulfonates (3) were successfully synthesized and characterized. X-ray studies and thermo-gravimetric analysis found that these complexes showed high anti-hydrolyzability and thermal stability. The high catalytic activity and excellent recyclability of these complexes were achieved in the Michael addition reaction and the allylation reaction. On account of their stability, storability, as well as catalytic efficiency, these complexes should find a broad range of utility in organic synthesis.

Ruthenium-catalyzed direct C3 alkylation of indoles with α,β-unsaturated ketones

In this paper, a simple and highly efficient ruthenium-catalyzed direct C3 alkylation of indoles with various α,β-unsaturated ketones without chelation assistance has been developed. This novel C-H activation methodology exhibits a broad substrate scope s

Highly effective and regioselective Michael addition of indoles to α,β-unsaturated ketones promoted by pentafluorophenylammonium triflate

A simple, inexpensive, environmentally friendly and efficient route for Michael addition of indoles to α,β-unsaturated ketones using pentafluorophenylammonium triflate (PFPAT) as a catalyst is described. Various indole derivatives were synthesized in good

Synthesis and structures of air-stable binuclear hafnocene perfluorobutanesulfonate and perfluorobenzenesulfonate and their catalytic application in C-C bond-forming reactions

The two air-stable m2-hydroxy-bridged binuclear hafnocene perfluorobutanesulfonate and perfluorobenzenesulfonate complexes were successfully synthesized. The high catalytic activity and recyclability of these complexes were exemplified for various carbon-carbon bond formation reactions. Compared with our previously reported hafnocene perfluorooctanesulfonate, these complexes show stronger Lewis acidity and better catalytic activity, and should find broad applications in organic synthesis.

Al-MCM-41 as a mild and ecofriendly catalyst for Michael addition of indole to α,β-unsaturated ketones

Mesoporous Al-MCM-41 catalyzes the chemoselective Michael addition reaction between indoles and α,β-unsaturated ketones to afford β-indolylketones at room temperature with excellent yields. The higher catalytic activity is attributed to Lewis acidic Al and the large surface area. The catalyst is readily recovered and reused more than six times without loss in its catalytic activity. The substitution at the indole nucleus occurs exclusively at the 3-position and N-alkylation products are not observed.

Metal halide hydrates as lewis acid catalysts for the conjugated Friedel-Crafts reactions of indoles and activated olefins

Metal halide hydrates such as SnCl2·2H2O, MnCl2·4H2O, SrCl2·6H 2O, CrCl2·6H2O, CoCl2· 6H2O e CeCl3·7H2O were investigated as mild Lewis acids catalysts for the conjugate Friedel-Crafts reaction between indoles and activated olefins. The reactions were carried out with aliphatic unsaturated ketones over a period of days at room temperature, while chalcones reacted only under reflux conditions. The reactions with nitrostyrenes were either performed in solvent or under solventless conditions. In all cases reasonable to good yields were obtained. ?2011 Sociedade Brasileira de Qui?mica.

Sulfamic acid as a cost-effective and recyclable solid acid catalyst for Friedel-Crafts alkylation of indole with α,β-unsaturated carbonyl compound and benzyl alcohol

Sulfamic acid was proved to be a cost-effective and recyclable catalyst for Friedel-Crafts type reaction of indole with α,β-unsaturated carbonyl compound and benzyl alcohol. Various indoles, α,β-unsaturated carbonyl compounds and a benzyl alcohol were suc