7126-64-9

Usage

Structure

A derivative of indole with a butyl group and a phenyl group attached to the indole ring

Usage

Commonly used in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds

Biological activities

Exhibits biological activities and is being studied for potential applications in drug discovery and development

Industrial applications

Also used in the production of fragrances and as a flavoring agent in the food industry

Versatility

A versatile chemical with many potential applications in various industries.

Upstream product

• 113675-25-5 acetophenone N-butylphenyl hydrazone 
• 109-65-9 1-bromo-butane 
• 583-11-9 N-(1-phenylethylidene)phenylhydrazine 
• 1643-19-2 tetrabutylammomium bromide 
• 6907-75-1 N-(1-phenylethylidene)butylamine 
• 583-53-9 2,3-dibromobenzene 
• 22014-99-9 N-butylindole 
• 591-50-4 iodobenzene 
• 583-55-1 1-Bromo-2-iodobenzene 
• 109-73-9 N-butylamine 
• 98-86-2 acetophenone 
• 542-69-8 1-iodo-butane 
• 13141-38-3 2-phenylethynylaniline 
• 4426-47-5 butylboronic acid 

Downstream Products

• 1585169-32-9 C₃₆H₃₆N₂O 

Relevant academic research and scientific papers

Water-medium C-H activation over a hydrophobic perfluoroalkane-decorated metal-organic framework platform

The use of water as reaction medium in the heterogeneous activation of C-H bonds has numerous advantages in terms of environmental benign, safety and cost efficiency impact. However, it is severely hampered because the reactants are difficult to dissolve in water and contact with the active sites of heterogeneous catalysts. Herein, we choose perfluoroalkane-functionalized mesoporous metal-organic framework (MOF) NU-1000 as a hydrophobic platform to encapsulate ultrafine palladium nanoparticles (Pd NPs) for C-H activation in water. The resultant Pd NPs stabilized by the perfluoroalkane exhibited high activity and regioselectivity in the direct C-H arylation of indoles in water. The introduction of perfluoroalkane chains into the mesoporous pores of NU-1000 provides hydrophobic surfaces to facilitate access of the reactants to the active sites to guarantee the high activity.

Cu(i)-catalyzed chemical fixation of CO2 with 2-alkynylaniline into 4-hydroxyquinolin-2(1H)-one

A copper(i) catalyzed reaction of 2-alkynylaniline with CO2 using DBU as base to produce 4-hydroxyquinolin-2(1H)-one derivatives in moderate to good yield is presented. In this reaction, a unique bond cleavage pattern for CO2 was observed that one of the C-O double bonds of CO 2 was totally broken and rearranged into two moieties in the absence of the reductive reagent. This efficient reaction system showed the wide generality of substrates including nitro, bromo, cyano and methoxylcarbonyl groups. A possible mechanism containing isocyanate intermediate is proposed. This journal is the Partner Organisations 2014.

One-pot approach to 1,2-disubstituted indoles via Cu(II)-catalyzed coupling/cyclization under aerobic conditions and its application for the synthesis of polycyclic indoles

A straightforward assembly of 1,2-disubstituted indoles has been developed through a Cu(II)-catalyzed domino coupling/cyclization process. Under aerobic conditions, a wide range of 1,2-disubstituted indole derivatives were efficiently and facilely synthesized from 2-alkynylanilines and boronic acids. 2-(2-Bromoaryl)-1-aryl-1H-indoles, which were selectively generated in one pot under the Cu catalysis, afforded the indolo[1,2-f]phenanthridines via Pd-catalyzed intramolecular direct C(sp2)-H arylation. The one-pot tandem approaches to the polycyclic indole derivatives were also successfully achieved.

Palladium nanoparticles encapsulated in a metal-organic framework as efficient heterogeneous catalysts for direct C2 arylation of indoles

Highly dispersed palladium nanoparticles (Pd NPs) encapsulated in the mesoporous cages of the metal-organic framework (MOF) MIL-101(Cr) have been prepared by using the wetness impregnation method. The Pd NPs were characterized by powder X-ray diffraction (PXRD), N2 adsorption, transmission electron microscopy, inductively coupled plasma atomic emission spectroscopy (ICP-AES), and X-ray photoelectron spectroscopy (XPS). The particles size ((2.6 ± 0.5) nm) of the obtained Pd NPs was in good agreement with the cage diameters (2.9 and 3.4 nm) of the MOF. The resulting Pd/MIL-101(Cr) catalyst exhibited extremely high catalytic activities in the direct C2 arylation of substituted indoles by using only 0.1 mol-% of the Pd catalyst. Moreover, the catalyst is easily recoverable and can be reused several times without leaching into solution and loss of activity. The combination of the highly dispersible Pd NPs within the accessible mesoporous cages and the favorable adsorption of the aryl halides on MIL-101 are suspected to be the main reasons for the observed high activities of the Pd/MIL-101(Cr) catalyst in the direct C2 arylation of indoles. MOF-encapsulated catalyst: Highly dispersed palladium nanoparticles encapsulated in the mesoporous metal-organic framework (MOF) MIL-101(Cr) exhibited high catalytic activities for the direct C2 arylation of substituted indoles with a range of substituted iodobenzenes (see figure) by only using a very low amount of the Pd catalyst (0.1 mol-%). The catalyst is easily recovered and can be reused several times without leaching into solution and loss of activity.

Modular synthesis of indoles from imines and o-dihaloarenes or o-chlorosulfonates by a Pd-catalyzed cascade process

A detailed study of the scope of a new Pd-catalyzed synthesis of indolesfrom 1,2-dihaloarenes and o-halobenzene sulfonates and imines is descri bed. The cascade reaction comprises an imine a-arylation ollowed by an intramolecular C-N bond-forming reaction promoted by the same Pd catalyst. The reaction with 1,2-dibromobenzene shows wide scope and allows the introduction of aryl, alkyl, and vinyl substituents at different positions of the five-membered ring of the indole. The regioselective synthesis of indoles substituted in the six-membered ring can be carried out by employing o-dihalobenzene derivatives with two different halogens, taking advantage of the different reactivities of I, Br, and Cl in oxidative addition reactions. This paper also introduces a method for the efficient cleavage of the N-t-butyl group, thus allowing for the preparation of N-H indoles through the same methodology. Finally, the reaction with o-halosulfonates has been studied. The best substrates are o-chlorononaflates, which lead to indoles in very high yield. The reaction is particularlyappropriate for the synthesis of the challenging 6-substituted indoles. In view of the availability of o-chlorophenols, which are direct precur sors of the chlorononaflates, this reaction represents an efficient entry into indoles substituted in the six-membered ring. The concept is illustrated by the preparation of a 4,6-disubstituted indole from naturally occurring anethole.

THERMAL INDOLIZATION AND "BASE CATALYSIS" IN THE E. FISCHER REACTION

Base catalysis cannot occur in the E.Fischer reaction.The possibility of a radical mechanism of thermal indolization was studied.It was shown that radical donors and acceptors do not affect the rate of the thermal process.

INDOLE DERIVATIVES. 121. CONVENIENT METHOD FOR THE PREPARATION OF N-ALKYLINDOLES

A new method was developed for the synthesis of N-alkylindoles from phenylhydrazones of aldehydes and ketones that makes it possible to obtain diverse N-alkylindoles under mild conditions.

A NEW MODIFICATION OF THE FISCHER REACTION. SYNTHESIS OF N-ALKYLINDOLES UNDER THE CONDITIONS OF EXTRACTIVE BASE CATALYSIS

A new modification of the Fischer reaction, which makes it possible to obtain 1-alkyl-, 1-alkyl-2-aryl, 1,3-dialkyl-, and 1,2,3-trialkylindoles under the conditions of interphase base catalysis, was developed.