69622-38-4

Upstream product

• 758640-21-0 N-Benzylaniline 
• 614-96-0 5-methyl-1H-indole 
• 98-88-4 benzoyl chloride 
• 145303-51-1 (5-methyl-1H-indol-1-yl)(phenyl)methanone 
• 611-73-4 Benzoylformic acid 
• 100-47-0 benzonitrile 
• 93-97-0 benzoic acid anhydride 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 3623-15-2 phenyl propargyl ketone 
• 106-49-0 p-toluidine 
• 63468-90-6 phenylglyoxylic acid potassium salt 

Downstream Products

• 1170354-47-8 (5-methyl-1-tosyl-1H-indol-3-yl)(phenyl)methanone 

Relevant academic research and scientific papers

Palladium-Catalyzed 2-fold C-H Activation/C-C Coupling for C4-Arylation of Indoles Using Weak Chelation

Palladium-catalyzed weak chelation-assisted regioselective C4-arylation of indoles has been accomplished using a readily available arene at moderate temperature. The C4-arylation, weak chelating benzoyl (Bz) directing group, cross-dehydrogenative coupling (CDC), broad substrate scope, and late-stage diversifications are the important practical features.

NbCl5 and AgClO4 promoted regio-selective acylation of indoles

In present study, an efficient and simple strategy towards chemo-selective and regio-selective acylation of indole using NbCl5 and AgClO4 catalyst are reported. This method utilizes the catalytic potentiality of NbCl5 and AgClO4 towards acylation of unprotected indoles in a synergistic manner. The combination of these catalytic system results into numerous advantages such as excellent yields of product, short reaction times and easier isolation of products.

Decarboxylative acylation of: N -free indoles enabled by a catalytic amount of copper catalyst and liquid-assisted grinding

A facile decarboxylative acylation of N-free indoles with α-ketonates via liquid-assisted grinding was reported. The reaction requires only a catalytic amount of Cu(OAc)2·H2O in combination with O2 as the terminal oxidant to give various 3-acylindoles with high efficiency. Additionally, this new methodology was applicable to a gram-scale synthesis.

Selective C-H acylation of indoles with α-oxocarboxylic acids at the C4 position by palladium catalysis

The first Pd-catalyzed direct C-H acylation of indoles at the C4 position with α-oxocarboxylic acids using a ketone directing group is described. This reaction exhibits high regioselectivity with the tolerance of a wide scope of functional groups to afford diverse acylated indoles in moderate-to-good yields. The control experiments evidence the generation of acyl radicals via K2S2O8 promoted decarboxylation of α-oxocarboxylic acids and the involvement of a PdII/PdIV catalytic cycle. Importantly, the synthetically useful selectivity observed might be applied to prepare indole derivatives with anti-tumor activity as tubulin inhibitors.

A novel synthesis of N-hydroxy-3-aroylindoles and 3-aroylindoles

A straightforward indole synthesis via annulation of C-nitrosoaromatics with conjugated terminal alkynones was realised achieving a simple, highly regioselective, atom- and step economical access to 3-aroylindoles in moderate to good yields. Further functionalizations of indole scaffolds were investigated and an easy way to JWH-018, a synthetic cannabinoid, was achieved.

Collective Synthesis of 3-Acylindoles, Indole-3-carboxylic Esters, Indole-3-sulfinic Acids, and 3-(Methylsulfonyl)indoles from Free (N-H) Indoles via Common N-Indolyl Triethylborate

A general and direct C3 functionalization of free (N-H) indoles with readily available electrophiles such as acid chlorides, chloroformates, thionyl chloride, and methylsulfonyl chloride via a common N-indolyl triethylborate intermediate is reported. The reaction proceeds smoothly under mild conditions in up to 93% yield. Indoles with substituents at the C2, C4, C5, C6, and C7 positions are well tolerated. The easy accessibility of a variety of important 3-acylindoles, indole-3-carboxylic esters, indole-3-sulfinic acids, and 3-(methylsulfonyl)indoles demonstrates the high degree of compatibility and practicability of this method.

Decarboxylative/decarbonylative C3-acylation of indoles: Via photocatalysis: A simple and efficient route to 3-acylindoles

A simple and efficient strategy for the preparation of 3-acylindoles via visible-light promoted C3-acylation of free (NH)- and N-substituted indoles with α-oxocarboxylic acids was developed. The reaction tolerates a wide range of functional groups, and the corresponding 3-acylindoles were obtained in high yields under mild conditions.

A simple, effective, green method for the regioselective 3-acylation of unprotected indoles

A fast and green method is developed for regioselective acylation of indoles in the 3-position without the need for protection of the NH position. The method is based on Friedel-Crafts acylation using acid anhydrides. The method has been optimized, and Y(OTf)3 in catalytic amounts is found to be the best catalyst together with the commercially available ionic liquid [BMI]BF4 (1-butyl-3-methylimidazolium tetrafluoro-borate) as solvent. The reaction is completed in a very short time using monomode microwave irradiation. The catalyst can be reused up to four times without significant loss of activity. A range of substituted indoles are investigated as substrates, and thirteen new compounds have been synthesized.

Palladium catalyzed addition of arylboronic acid or indole to nitriles: Synthesis of aryl ketones

Aryl ketones can be synthesized conveniently by a palladium catalyzed addition of arylboronic acid to nitriles in aqueous triflic acid. This catalytic system was extended to the addition of unprotected indoles to nitriles under a slightly modified condition to produce 3-acyl indoles in good yields.

Copper-catalyzed decarboxylative C3-acylation of free (N-H) indoles with α-oxocarboxylic acids

An efficient Cu-catalyzed decarboxylative C3-acylation of free (N-H) indoles using α-oxocarboxylic acids as acylating agents has been developed. This method was compatible with a variety of functional groups and provided an attractive alternative access to 3-acylindoles in moderate to high yields.