221910-17-4

Upstream product

• 13329-40-3 4-Iodoacetophenone 
• 201230-82-2 carbon monoxide 
• 103529-16-4 2-[(trimethylsilyl)ethynyl]aniline 
• 52670-38-9 2-ethynylaniline 
• 99-90-1 para-bromoacetophenone 
• 615-43-0 2-iodophenylamine 
• 42472-69-5 4-ethynylacetophenone 

Downstream Products

• 201813-48-1 N-{2-[(4-acetylphenyl)ethynyl]phenyl}-2,2,2-trifluoroacetamide 
• 1200688-15-8 C₁₇H₁₃NO₂ 
• 1570214-68-4 1-(4-(3,3-difluoro-3H-indol-2-yl)phenyl)ethanone 
• 1558818-21-5 C₂₅H₂₀O₃ 
• 1415694-11-9 1-(4-((2-iodophenyl)ethynyl)phenyl)ethan-1-one 
• 1558817-53-0 C₂₅H₂₀O₃ 
• 1374309-28-0 dimethyl 4-(4-acetylbenzoyl)quinoline-2,3-dicarboxylate 
• 1374309-40-6 C₂₇H₂₁NO₄ 
• 1374336-95-4 C₂₇H₂₇NO₃ 
• 1236003-90-9 (Z)-1-(4-((2-(dimethylamino)-4H-benzo[d][1,3]thiazin-4-ylidene)methyl)phenyl)ethanone 
• 1213786-08-3 1-(4-(3-(phenylthio)-1H-indol-2-yl) phenyl)ethanone 

Relevant academic research and scientific papers

Palladium-Catalyzed Ligand-Free Double Cyclization Reactions for the Synthesis of 3-(1′-Indolyl)-phthalides

Indole and phthalide are privileged heterocyclic scaffolds in numerous natural products and bioactive molecules. The synthesis and biological evaluation of the compounds combining these two scaffolds have rarely been reported. Herein, we repot the first palladium-catalyzed ligand-free double cyclization reactions that enable efficient synthesis of 3-(1′-indolyl)-phthalides (42 examples, up to 96% yield) under mild conditions. Notably, only 1.0 mol % of catalyst loading is used, suggesting high efficiency. Late-stage elaborations give highly functionalized analogues.

One-Pot Synthesis of N-Imidoyl-(1 H)-indoles via Palladium-Catalyzed Oxidative Insertion Domino Reaction with Isocyanide and Arylboronic Acid

Efficient one-pot synthesis of N-imidoyl-(1H)-indoles has been described, which is achieved by the palladium-catalyzed oxidative insertion of 2-(phenylethynyl)aniline, arylboronic acid, and isonitrile. This method provides a new way to synthesize N-imidoy

[3+2]-Annulation of platinum-bound azomethine ylides with distal C=C bonds of N-allenamides

A Pt-catalyzed, highly regioselective reaction between N-allenamides and imino-alkynes leading to pyrrolo[1,2-a]indoles is described. This represents the first example of [3+2]-annulation of Pt-bound azomethine ylides with the distal C=C bond of N-allenam

Silver-catalyzed one-pot cyclization/fluorination of 2-alkynylanilines: Highly efficient synthesis of structurally diverse fluorinated indole derivatives

Highly efficient approaches to obtain structurally diverse fluorinated indole derivatives have been realized through the Ag-catalyzed one-pot cyclization/fluorination of 2-alkynylanilines in the presence of NFSI or Selectfluor. The Royal Society of Chemistry.

Palladium complexes derived from N,N-bidentate NH-iminophosphorane ligands: Synthesis and use as catalysts in the Sonogashira reaction

The addition of primary amines to the CC bond of diphenylalkenyl iminophosphoranes yielded a new subtype of N,N-bidentate ligands bearing NP V-C-C-NH backbones. These donor ligands reacted with PdCl 2(COD) to give the corresponding σ

Ready synthesis of free N-H 2-arylindoles via the copper-catalyzed amination of 2-bromo-arylacetylenes with aqueous ammonia and sequential intramolecular cyclization

A wide range of free N-H 2-arylindoles were synthesised via the copper(ii)-catalyzed amination of 2-bromo-arylacetylenes with aqueous ammonia and sequential intramolecular cyclization. The convenience and atom economy of aqueous ammonia, and the low cost of the copper catalytic system make this protocol readily superior in practical application. The Royal Society of Chemistry 2011.

Synthesis of 2-alkoxy(aroxy)-3-substituted Quinolines by DABCO-promoted cyclization of o-alkynylaryl isocyanides

Diversified 2-alkoxy- and 2-aroxy-3-substituted quinolines were synthesized from o-alkynylaryl isocyanides and alcohols and phenols promoted by DABCO, respectively. The reaction was initiated by nucleophilic addition of DABCO to isocyanide and subsequent

3-(2-Alken-1-one-2-yl)indoles through the palladium-catalyzed reaction of 2-alkynyltrifluoroacetanilides with cyclic α-iodoenones

α-Iodoenones can be efficiently employed as organic electrophiles in the Pd-catalyzed synthesis of 2,3-disubstituted indoles from 2-alkynyltrifluoroacetanilides. Best results were obtained using the weak ligand As(Ph)3. The methodology reported provides an efficient entry to indoles bearing a 2-alkenon-2-yl moiety linked in the 3-position, that possesses a scarcely reported substitution pattern.

Sonogashira cross-coupling reactions and construction of the indole ring system using a robust, silica-supported palladium catalyst

The use of a recyclable silica-supported palladium catalyst in Sonogashira couplings and indole syntheses using a range of functionalised substrates is described. The catalyst is shown to be both robust and versatile, effecting the synthesis of 2-phenylindole in quantitative yield without the need for N-protection, a copper co-catalyst, a base, or a solvent. Georg Thieme Verlag Stuttgart.

The palladium-catalyzed transfer hydrogenation/heterocyclization of β- (2-aminophenyl)-α,β-ynones. An approach to 2-aryl- and 2-vinylquinolines

The palladium-catalyzed transfer hydrogenation/cyclization of readily available β-(o-aminophenyl)-α,β-ynones I affords 2-aryl- and 2- vinylquinolines 3 in good yield.