1401518-60-2

Upstream product

• 37952-94-6 N-(4-methylbenzoyl) saccharin 
• 3419-91-8 N-(2-pyridyl)indole 
• 874-60-2 4-methyl-benzoyl chloride 
• 120-72-9 indole 
• 109-04-6 2-bromo-pyridine 
• 624-31-7 4-tolyl iodide 
• 106-38-7 para-bromotoluene 
• 6631-37-4 2-(phenylamino)pyridine 
• 504-29-0 2-aminopyridine 
• 591-50-4 iodobenzene 
• 106-43-4 para-chlorotoluene 
• 4209-24-9 p-methylphenacyl chloride 
• 62-53-3 aniline 
• 89108-49-6 1-(1-azidovinyl)-4-methyl benzene 

Downstream Products

• 55577-25-8 2-(4-methylphenyl)-1H-indole 

Relevant academic research and scientific papers

Copper-Catalyzed Direct Arylation of Indoles and Related (Hetero)arenes: A Ligandless and Solvent-free Approach

A ligandless and solvent-free copper-catalyzed method for the regioselective C?H bond arylation of indoles and related heteroarenes is reported. The use of CuCl efficiently catalyzes the direct coupling of diverse heteroarenes with aryl iodides via chelation-assistance. This reaction could tolerate sensitive and structurally diverse functionalities, including halides, ethers, thioethers, amines, indolyl, pyrrolyl and carbazolyl groups. The directing group, 2-pyridinyl can be smoothly removed to generate C-2 arylated free-NH indoles, and the arylated indoles can further be functionalized into Tryptamine derivatives. Preliminary mechanistic study revealed a radical pathway for the arylation reaction. (Figure presented.).

Iridium(III)-Catalyzed Tandem Annulation of Pyridine-Substituted Anilines and α-Cl Ketones for Obtaining 2-Arylindoles

A facile and expeditious protocol for the synthesis of 2-arylindole compounds from readily available N-(2-pyridyl)anilines and commercially available α-Cl ketones through iridium-catalyzed C-H activation and cyclization is reported here. As a complementary approach to the conventional strategies for indole synthesis, the transformation exhibits powerful reactivity, tolerates a large number of functional groups, and proceeds with good to excellent yields under mild conditions, providing a straightforward method to obtain structurally diverse and valuable indole scaffolds. Furthermore, the reaction could be easily scaled up to gram scale.

Nickel-Catalyzed C(2)-H Arylation of Indoles with Aryl Chlorides under Neat Conditions

Nickel-catalyzed regioselective C(2)-H arylation of indoles and pyrroles with aryl chlorides is achieved under neat conditions. This method allows the efficient coupling of diverse aryl chlorides employing a user-friendly and inexpensive Ni(OAc)2/su

Nickel-Catalyzed Intramolecular Coupling of Sulfones via the Extrusion of Sulfur Dioxide

We describe a method for intramolecular desulfonylative coupling using bis(cyclooctadiene)nickel as a catalyst. A broad range of aromatic, heteroaromatic and aliphatic sulfones can be utilized as substrates in this process. This method provides an atom-economical route to the synthesis of various biaryls and an efficient tool for the catalytic conversion of sulfonyl groups, representing a significant advancement in organic synthesis. (Figure presented.).

Synthesis of 2-substituted indoles by iridium (III)-catalyzed C–]H functionalization of N-phenylpyridin-2-amines

A highly regioselective synthesis of 2-substituted indoles was realized through Ir(III)-catalyzed C–]H functionalization of N-phenylpyridin-2-amines followed by the reaction with sulfoxonium ylides and intramolecular cyclization under mild conditions. The reaction completed with broad range of substrate scopes and gave various 2-substituted indoles in up to 98% yields.

Rhodium(III)-catalyzed intermolecular cyclization of anilines with sulfoxonium ylides toward indoles

Rhodium(III)-catalyzed synthesis of indole derivatives has been realized via cascade reaction of C–H alkylation/nucleophilic cyclization starting from readily available N-phenylpyridin-2-amines and sulfoxonium ylides. Notably, this transformation could smoothly proceed with high yields, good regioselectivity, and feature broad group tolerance and under redox-neutral condition to avoid external oxidant. The titled products are potentially important building blocks in the organic synthesis through various chemical transformations.

Ruthenium-catalyzed synthesis of indole derivatives from: N -aryl-2-aminopyridines and alpha-carbonyl sulfoxonium ylides

Indole is a ubiquitous structural motif with important applications in many areas of chemistry. Given this, a simple and efficient Ru(ii)-catalyzed synthesis of indole via intermolecular annulation of N-aryl-2-aminopyridines and sulfoxonium ylides was proposed and accomplished. Excellent selectivity and good functional group tolerance of this transformation were observed. This protocol provides easy access to a wide variety of useful indoles in the presence of a commercially available [Ru(p-cymene)Cl2]2 catalyst. A possible mechanism for the reaction pathway was also proposed. More importantly, this reaction will offer a useful method for the construction of enantioenriched indole frameworks.

Synthesis of 2-Arylindoles through Pd(II)-Catalyzed Cyclization of Anilines with Vinyl Azides

Vinly azides are featured as electrophiles, nucleophiles, and radical acceptors in synthetic chemistry and have emerged as rapid and versatile synthons in the preparation of N-heterocyclic systems. Herein, a novel approach to 2-arylindoles via Pd(II)-catalyzed cyclization reaction of anilines with vinyl azides has been achieved, which furnishes the versatile 2-arylindoles with high efficieny and excellent regioselectivity.

Expeditious and Solvent-Free Nickel-Catalyzed C?H Arylation of Arenes and Indoles

An efficient solvent-free nickel-catalyzed method for C?H bond arylation of arenes and indoles has been developed, which proceeds expeditiously through chelation assistance. The reaction is highly selective for mono-arylation and tolerates sensitive and structurally diverse functionalities, such as halides, ethers, amines, indole, pyrrole and carbazole. This reaction represents the first example of a nickel-catalyzed C?H arylation by monochelate assistance and symbolizes a rare precedent in solvent-free C?H arylation. Mechanistic investigations by various controlled reactions, kinetic studies, and deuterium labeling experiments suggest that the arylation follows a single electron transfer (SET) pathway involving the turnover-limiting C?H nickelation process.