960608-47-3

Upstream product

• 6828-35-9 5-chloro-2-iodoaniline 
• 536-74-3 phenylacetylene 
• 106-47-8 4-chloro-aniline 
• 1262543-88-3 2-bromo-4-chloro-1-(phenylethynyl)benzene 
• 89-63-4 4-Chloro-2-nitroaniline 
• 5446-05-9 4-chloro-2-nitroiodobenzene 

Downstream Products

• 1333392-23-6 2-azido-4-chloro-1-(phenylethynyl)benzene 
• 1374753-84-0 6-chloro-2-phenyl-1-(p-toluenesulfonyl)indole 
• 1236044-92-0 N-(5-chloro-2-(phenylethynyl)phenyl)-4-methylbenzenesulfonamide 
• 1026644-34-7 4-(6-chloro-2-phenyl-1H-indol-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Copper(I)-Mediated Cascade Annulation via Dual C-H/C-H Activation: Access to Benzo[a]carbazolic AEEgens

A Cu(I)-mediated cascade cyclization/annulation of unprotectedo-alkynylanilines with maleimides in one pot is developed. The protocol offers sequential formation of one C-N and two C-C bonds to deliver fused benzo[a]carbazoles having free NH skeletons. The annulated products display fluorescence emission in the range of 485-502 nm with a large Stokes shift and fluorescence lifetime of ～17 ns. The annulated3aadisplays AEE behavior in the ethanol/hexane system and possesses marigold-flower-like morphology at the aggregated state. Cell viability assays enumerate biocompatible AEEgens, while their high intracellular fluorescence depicts cell imaging applicability.

Gold(I)-Catalyzed Reactions between N-(o-Alkynylphenyl)imines and Vinyldiazo Ketones to Form 3-(Furan-2-ylmethyl)-1 H-indoles via Postulated Azallyl Gold and Allylic Cation Intermediates

This work describes gold-catalyzed additions of vinyldiazo ketones to N-(o-alkynylphenyl)imines to yield 3-(furan-2-ylmethyl)-1H-indoles involving skeletal rearrangement; these new catalytic reactions are applicable to a wide range of substrates. We postu

Asymmetric Synthesis of 3-Methyleneindolines via Rhodium(I)-Catalyzed Alkynylative Cyclization of N-(o-Alkynylaryl)imines

The first asymmetric synthesis of 3-methyleneindolines from alkynyl imines has been developed via a rhodium-catalyzed tandem process: regioselective alkynylation of the internal alkynes and subsequent intramolecular addition to the imines. The reaction pr

Nickel-catalyzed cyclization of 1,7-enynes for the selective synthesis of dihydrocyclobuta[c]quinolin-3-ones and benzo[b]azocin-2-ones

We herein described a nickel-catalyzed cyclization ofN-(o-ethynylaryl)acrylamides for the selective synthesis of dihydrocyclobuta[c]quinolin-3-ones and benzo[b]azocin-2-ones. The two varied products could be easily obtained by tuning the reaction temperature. This reaction features easy temperature-control, high efficiency, and gram-scale synthesis.

Copper-Catalyzed Aerobic Oxidative Cyclization of 2-Alkynylanilines with Nitrosoarenes: Synthesis of Organic Solid Mechanoluminescence Compounds of 4-Oxo-4 H-cinnolin-2-ium-1-ide

An efficient Cu(I)/DMAP/air system for the one-pot synthesis of 4-oxo-4H-cinnolin-2-ium-1-ides, which are often difficult to prepare by traditional routes from substituted 2-alkynylanilines and nitrosoarenes, was developed. These 4-oxo-4H-cinnolin-2-ium-1-ides have practical applications as mechanoluminescent materials. Preliminary mechanistic experiments were performed, and a plausible mechanism for this tandem process is proposed. The use of an inexpensive copper catalyst and molecular oxygen as the oxygen source and the oxidant make this an attractive green protocol with potential synthetic applications.

A competitive and highly selective 7-, 6- And 5-annulation with 1,3-migration through C-H and N-H-alkyne coupling

We demonstrated a highly competitive and selective C-C and N-C cross-coupled 7-, 6- and 5-annulation utilizing 2-ethynylanilides to afford functionalized 1H-benzo[b]azepin-2(5H)-ones, 2-quinolinones, and 3-acylindoles in high yield. ZnCl2 was f

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 Copper-Catalyzed Cascade Bicyclization Strategy for Synthesis of 2-(1H-Indol-1-yl)-4,5-dihydrothiazoles and 2-(1H-Indol-1-yl)thiazol-5-yl Aryl Ketones with Molecular Oxygen as an Oxygen Source

An atom-economical method for synthesizing N-heterocyclic indoles from readily available o-alkynylphenyl isothiocyanates and propargylamine derivatives is reported. This method involves a copper-catalyzed cascade bicyclization process consisting of an int

Photoredox Decarboxylative Alkylation/(2+2+1) Cycloaddition of 1,7-Enynes: A Cascade Approach Towards Polycyclic Heterocycles Using N-(Acyloxy)phthalimides as Radical Source

No Abstract. (Figure presented.).

Gold-catalyzed tandem reaction of 2-alkynylanilines followed by 1,6-conjugate addition to: P -quinone methides: Efficient access to unsymmetrical diarylindolylmethanes

A simple, mild, efficient and chemoselective catalytic method for the straightforward synthesis of an interesting class of 2-aryl/alkyl-substituted-3-diaryl indolyl methanes in high yield is reported. This atom-efficient method proceeds via a gold-catalyzed one-pot sequential intramolecular hydroamination (C-N bond formation) of 2-alkynylanilines followed by a 1,6-conjugate addition to p-quinonemethides. The p-quinonemethides, which contain aldehyde functional groups, preferentially participate in 1,6-conjugate addition, while the aldehyde functional group remains unreactive.