5782-23-0

Upstream product

• 90141-86-9 4-(4'-methoxyphenyl)cinnoline 
• 696-62-8 para-iodoanisole 
• 143360-93-4 N-(2-ethynylphenyl)-2,2,2-trifluoroacetamide 
• 120-72-9 indole 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 100-65-2 N-Phenylhydroxylamine 
• 768-60-5 4-methoxyphenylacetylen 
• 1006-94-6 5-methoxylindole 
• 5703-26-4 4-Methoxyphenylacetaldehyde 
• 100-63-0 phenylhydrazine 
• 577-19-5 2-nitrophenyl bromide 
• 32117-52-5 1-(1-(4-methoxyphenyl)ethylidene)-2-tosylhydrazine 
• 65185-68-4 o-bromonitrostyrene 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 51206-77-0 3-(4-methoxyphenyl)-1-methyl-1H-indole 
• 1288963-89-2 2-(3,5-dimethylisothiazol-4-yl)-3-(4-hydroxyphenyl)-1H-indole-1-carbonitrile 
• 1288963-86-9 2-(3,5-dimethylisothiazol-4-yl)-3-(4-methoxyphenyl)-1H-indole-1-carbonitrile 
• 1288963-85-8 2-bromo-3-(4-methoxyphenyl)-1H-indole-1-carbonitrile 
• 1288963-61-0 2-(3,5-dimethylisothiazol-4-yl)-3-(4-hydroxyphenyl)-1H-indole-1-carboxamide 
• 1288963-60-9 2-(3,5-dimethylisothiazol-4-yl)-N'-hydroxy-3-(4-hydroxyphenyl)-1H-indole-1-carboximidamide 
• 1288963-75-6 2-(3,5-dimethylisoxazol-4-yl)-N-ethyl-3-(4-methoxyphenyl)-1H-indole-1-carboxamide 
• 1288963-19-8 2-(3,5-dimethylisoxazol-4-yl)-N-ethyl-3-(4-hydroxyphenyl)-1H-indole-1-carboxamide 
• 1288963-04-1 2-(3,5-dimethyIisoxazol-4-yl)-3-(4-hydroxyphenyl)-1H-indole-1-carbonitrile 
• 1288963-73-4 2-(3,5-dimethylisoxazol-4-yl)-3-(4-hydroxyphenyl)-1H-indole-1-carbaldehyde 

Relevant academic research and scientific papers

Pd/β-cyclodextrin-catalyzed C-H functionalization in water: A greener approach to regioselective arylation of (NH)-indoles with aryl bromides

A greener and more practical strategy for the site-selective C-H arylation of (NH)-indoles via coupling of (hetero)aryl bromides was developed, in which β-cyclodextrin, acting as both a ligand for Na2PdCl4 and a host for indoles, enables the reactions to occur easily in water. The key advantage of this method is the ingenious merging of aqueous homogeneous catalysis and ligand mediation, leading to the highly regioselective formation of C3-arylindoles with a broad substrate scope and functional-group tolerance. Moreover, the regioselectivity can be switched from the C3 to the C2-position by varying the nature of the base without recourse to employing ArI as substrates.

Synthesis and antimycobacterial activity of 3-phenyl-1h-indoles

Tuberculosis has been described as a global health crisis since the 1990s, with an estimated 1.4 million deaths in the last year. Herein, a series of 20 1H-indoles were synthesized and evaluated as in vitro inhibitors of Mycobacterium tuberculosis (Mtb) g

Acid mediated coupling of aliphatic amines and nitrosoarenes to indoles

Traditionally, amines react with nitrosoarenes to provide the corresponding imines or azo compounds. Herein, we report an acid mediated annulation reaction of aliphatic amines and nitrosoarenes to provide indole derivatives. The elusive direct annulation of aliphatic amines and nitrosoarenes via simultaneous C-C and C-N bond formation was achieved under metal free conditions. This conceptually novel method for indole synthesis does not require pre-functionalization steps for the new C-C and C-N bond formation. The method has been applied for an elegant synthesis of nor-neocryptolepine and neocryptolepine.

Structure Ligation Relationship of Amino Acids for the Selective Indole C?H Arylation Reaction: L-Aspartic acid as Sustainable Alternative of Phosphine Ligands

The Structure Ligation Relationship (SLR) of free amino acids (AAs) under Pd-catalysis were examined for the chemo- and regio-selective indole C?H arylation reactions. While the majority of AAs were minor or ineffective, the L-aspartic acid (L-Asp) stands out promising to deliver high-value C3-arylated indoles with excellent chemo- (C vs N) and regioselectivity (C3 vs C2) with high functional group tolerance. Thus, the protocol offers a cost-effective and sustainable alternative of phosphine-based ligands for the indole C3?H arylation reactions. Preliminary mechanistic investigations suggested the simultaneous involvement of ?NH2, α-CO2H, and β-CO2H functionalities of L-Asp and found critical for its ligation efficiency. The developed catalytic system was compatible with the tandem decarboxylation/arylation procedure for the chemoselective synthesis of 3-aryl indoles. (Figure presented.).

Direct C3-Selective Arylation of N-Unsubstituted Indoles with Aryl Chlorides, Triflates, and Nonaflates Using a Palladium-Dihydroxyterphenylphosphine Catalyst

A palladium-dihydroxyterphenylphosphine (DHTP) catalyst was successfully applied to the direct C3-arylation of N-unsubstituted indoles with aryl chlorides, triflates, and nonaflates. This catalyst showed C3-selectivity, whereas catalysts with other structurally related ligands exhibited N1-selectivity. Complex formation between the lithium salts of the ligand and the indole is assumed to accelerate the arylation at the C3 position. Reactions using 3-alkylindoles afforded 3,3-disubstituted indolenines, which can be further converted to the corresponding indoline derivatives.

Regiospecificity in Ligand-Free Pd-Catalyzed C-H Arylation of Indoles: LiHMDS as Base and Transient Directing Group

A highly efficient catalyst-base pair for the C-H arylation of free (NH)-indoles in the C-3 position is reported. Ligand-free palladium acetate coupled with lithium hexamethyldisilazide (LiHMDS) catalyzed the regiospecific, i.e. 100% regioselective, C-3 a

A micellar catalysis strategy applied to the Pd-catalyzed C-H arylation of indoles in water

The selective control over multiple competing C-H sites would enable straightforward access to functionalized indoles. In this context, we report here a modular and selective C-H arylation of indoles following the micellar catalysis approach using the third generation "designer" surfactant SPGS-550-M in the presence of 1 mol% of [(cinnamyl)PdCl]2 under mild conditions. Thus, access to high value C-arylated (C-3 and C-2) indoles was achieved fulfilling the "triple bottom line philosophy" of green chemistry. The nature of the phosphine ligand was found to be critical for achieving site-selectivity, DPPF and DPPP being the most effective in promoting the arylation at C3-H and C2-H, respectively. The reaction is scalable and offers high chemo- (C vs. N) and regio-selectivity (C-3 vs. C-2) with a wide range of functional group tolerance. The surfactant aqueous solution can be recycled and reused without compromising on product yields.

Catalytic Au(i)/Au(iii) arylation with the hemilabile MeDalphos ligand: Unusual selectivity for electron-rich iodoarenes and efficient application to indoles

The ability of the hemilabile (P,N) MeDalphos ligand to trigger oxidative addition of iodoarenes to gold has been thoroughly studied. Competition experiments and Hammett correlations substantiate a clear preference of gold for electron-enriched substrates both in stoichiometric oxidative addition reactions and in catalytic C-C cross-coupling with 1,3,5-trimethoxybenzene. This feature markedly contrasts with the higher reactivity of electron-deprived substrates typically encountered with palladium. Based on DFT calculations and detailed analysis of the key transition states (using NBO, CDA and ETS-NOCV methods in particular), the different behavior of the two metals is proposed to result from inverse electron flow between the substrate and metal. Indeed, oxidative addition of iodobenzene is associated with a charge transfer from the substrate to the metal at the transition state for gold, but opposite for palladium. The higher electrophilicity of the gold center favors electron-rich substrates while important back-donation from palladium favors electron-poor substrates. Facile oxidative addition of iodoarenes combined with the propensity of gold(iii) complexes to readily react with electron-rich (hetero)arenes prompted us to apply the (MeDalphos)AuCl complex in the catalytic arylation of indoles, a challenging but very important transformation. The gold complex proved to be very efficient, general and robust. It displays complete regioselectivity for C3 arylation, it tolerates a variety of functional groups at both the iodoarene and indole partners (NO2, CO2Me, Br, OTf, Bpin, OMe?) and it proceeds under mild conditions (75 °C, 2 h).

Photoredox Cyanomethylation of Indoles: Catalyst Modification and Mechanism

The direct cyanomethylation of indoles at the 2- or 3-position was achieved via photoredox catalysis. The versatile nitrile synthon is introduced as a radical generated from bromoacetonitrile, a photocatalyst, and blue LED as a light source. The mechanism of the reaction is explored by determination of the Stern-Volmer quenching constants. By combining photophysical data and mass spectrometry to follow the catalyst decomposition, the catalyst ligands were tuned to enable synthetically useful yields of radical coupling products. A range of indole substrates with alkyl, aryl, halogen, ester, and ether functional groups participate in the reaction, affording products in 16-90% yields. The reaction allows the rapid construction of synthetically useful cyanomethylindoles, products that otherwise require several synthetic steps.

Structure-Modified Germatranes for Pd-Catalyzed Biaryl Synthesis

Germanium, a member of 14th group that falls between Si and Sn, has remained considerably ignored as a nucleophile for a long time. Compared with other forms of Ge-containing nucleophiles, germatranes are structure-defined, easily accessible, and stabilized nucleophilic fragments, but they fail to meet the need of high reactivity and facile introducing to organics. Herein, we report a modified structure of germatranes, whose cross-coupling reactivity is greatly improved. The structure can be easily constructed from inexpensive industrial GeO2, and corresponding Ge-Cl and Ge-H can also be obtained after facile transformations. Moreover, Ar-Ge can be effectively synthesized either from Grignard reagents or Pd-catalyzed germylation of aryl halides.