878133-02-9

Upstream product

• 440363-04-2 2-(2-trimethylsilylethynyl)-4-trifluoromethylaniline 
• 163444-17-5 2-iodo-4-(trifluoromethyl)aniline 
• 1066-54-2 trimethylsilylacetylene 
• 57946-63-1 4-amino-3-bromobenzotrifluoride 
• 455-14-1 4-trifluoromethylphenylamine 
• 878133-04-1 2,2,2-trifluoro-N-(2-iodo-4-(trifluoromethyl)phenyl)acetamide 

Downstream Products

• 100846-24-0 5-trifluoromethyl-1H-indole 
• 491601-38-8 2-phenyl-5-(trifluoromethyl)-1H-indole 
• 1223577-66-9 2,3-diphenyl-5-(trifluoromethyl)-1H-indole 
• 57799-43-6 1-(2-amino-5-(trifluoromethyl)phenyl)ethanone 
• 1040204-08-7 N-(2-ethynyl-4-(trifluoromethyl)phenyl)methanesulfonamide 

Relevant academic research and scientific papers

Sequential Sonogashira/intramolecular aminopalladation/cross-coupling ofortho-ethynyl-anilines catalyzed by a single palladium source: rapid access to 2,3-diarylindoles

We have developed a practical and efficient one-pot protocol for the synthesis of 2,3-diarylindolesviaPd-catalyzed bis-arylative cyclization of variouso-ethynylanilines with aryl iodides. Mechanism studies showed that a Pd-catalyzed Sonogashira reaction took place firstly, giving an internal alkyne intermediate, which subsequently underwent intramolecular aminopalladation/cross-coupling to give access to 2,3-diarylindoles. The present methodology exhibits a broad substrate scope, producing various 2,3-diaryl indoles bearing two different aryl groups.

New indolo[1,2-c]quinazolines for single-crystal field-effect transistor: A united experimental and theoretical studies

Here, we account the synthesis and characterization of a series of symmetrical fused heterocyclic aromatic hydrocarbons (HAHs) with an indolo[1,2-c]quinazoline (IQ) as the core moiety. All the new HAHs IQ series were systematically investigated by using various spectroscopic methods. Furthermore, their photo-physical properties were supported by density functional theory (DFT) and time-dependent density functional theory (TDDFT) studies to support the experimental findings. The tetramethyl-substituted indolo[1,2-c]quinazoline (TMIQ) compound is shown to exhibit the shifted type of π–π stacking interactions, which render this series as a new semiconducting material. Single-crystal-based field-effect transistor devices of TMIQ exhibited efficient charge transport behavior, giving a p-channel field-effect mobility of 0.25 cm2?V?1?s?1 with an on/off ratio of 5 × 105.

Copper-Catalyzed Enantioselective C-H Arylation between 2-Arylindoles and Hypervalent Iodine Reagents

The copper-catalyzed enantioselective C-H arylation between 2-arylindoles and hypervalent iodine reagents has been successfully developed, which provides a convenient and economical route to the highly atroposelective synthesis of axially chiral indole de

Copper-Catalyzed Chemoselective Cyclization Reaction of 2-Isocyanoacetophenone: Synthesis of 4-Hydroxyquinoline Compounds

A copper-catalyzed intramolecular cyclization reaction of 2-isocyanoacetophenone derivatives to afford 4-hydroxyquinolines chemoselectively is described. The transformation proceeds through enol tautomerism and a subsequent C-C bond formation. Compared to previous methods, this study provides a new protocol for the construction of 4-hydroxyquinoline compounds from functionalized isocyanides under mild conditions.

Palladium-Catalyzed Enantioselective Cacchi Reaction: Asymmetric Synthesis of Axially Chiral 2,3-Disubstituted Indoles

We report herein the first examples of a palladium-catalyzed enantioselective Cacchi reaction for the synthesis of indoles bearing a chiral C2-aryl axis. In the presence of a catalytic amount of Pd(OAc)2 and (R,R)-QuinoxP* ligand, reaction of N-aryl(alkyl)sulfonyl-2-alkynylanilides with arylboronic acids under oxygen atmosphere afforded enantioenriched 2,3-disubstituted indoles in high yields and enantioselectivity. The indole ring is constructed de novo in this process and a complexation-induced chirality transfer is proposed to account for the observed enantioselectivity.

Optimizing ligand structure for low-loading and fast catalysis for alkynyl-alcohol and-amine cyclization

A series of [Ru(Cp/Cp?)(PR2NR′2)(MeCN)]PF6 complexes were prepared, in which the steric and electronic properties of the primary coordination sphere were varied (R = Ph, t-Bu, Bn; and Cp vs. Cp?). These complexes were catalytically active in the cyclization of alkyne substrates with an intramolecular nucleophile (amine or alcohol) to produce 5-and 6-membered heterocycles. The effect of the 1° coordination sphere structure on catalyst performance was evaluated. Steric bulk around the metal centre was a key feature to achieve rapid catalysis at low temperatures. The catalyst [Ru(Cp)(Pt-Bu2NPh2)(MeCN)]PF6 gave a turnover number that was >1 order of magnitude more active than previous catalysts in the cyclization of the benchmark substrate 2-ethynylaniline. This catalyst is tolerant of a diversity of functional groups and is competent at the formation of various substituted indoles.

Copper-Catalyzed Tandem Cross-Coupling/[2 + 2] Cycloaddition of 1,6-Allenynes with Diazo Compounds to 3-Azabicyclo[5.2.0] Ring Systems

An unprecedented copper-catalyzed tandem cross-coupling/[2 + 2] cycloaddition of 1,6-allenynes with diazo compounds was reported, chemo- and regioselectively providing 3-azabicyclo[5.2.0] frameworks in moderate to excellent yields under mild reaction conditions. Moreover, the products readily convert to highly functionalized quinolines via oxidative radical rearrangement.

Synthesis of 2-(Trifluoromethyl)indoles via Domino Trifluoromethylation/Cyclization of 2-Alkynylanilines

A new method for the synthesis of 2-(trifluoromethyl)indoles using easily accessible 2-alkynylanilines and a well-established fluoroform-derived CuCF3 reagent is described. This method utilizes a domino trifluoromethylation/cyclization strategy

Gold-Catalyzed Intermolecular [4+2] Annulation of 2-Ethynylanilines with Ynamides: An Access to Substituted 2-Aminoquinolines

A gold-catalyzed intermolecular [4+2] annulation of easily accessible 2-ethynylanilines with ynamides offers a highly region-selective, modular, efficient, and atom-economical strategy for the synthesis of substituted 2-aminoquinolines in up to 93% yield. (Figure presented.).

One-Pot Access to Benzo[a]carbazoles via Palladium(II)-Catalyzed Hetero- and Carboannulations

A Pd(II)-catalyzed direct synthesis of benzo[a]carbazoles has been achieved through aminopalladation of alkynes, followed by intramolecular nucleophilic addition of the generated carbon-palladium bond to a tethered cyano/aldehyde group. Compared to literature procedures, this synthetic approach is operationally simple, uses simple substrates, and offers a fast intramolecular assembly resulting in the direct synthesis of benzo[a]carbazoles in which a wide variation of substituents at different sites is well-tolerated, leaving enough opportunity for diversification.