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Upstream product

• 120-72-9 indole 
• 873-73-4 4-n-chlorophenylacetylene 
• 3240-10-6 (4-chlorophenyl)propiolic acid 
• 1073-67-2 4-vinylbenzyl chloride 
• 208118-80-3 1-(4-chlorophenyl)ethenylacetamide 
• 99-91-2 para-chloroacetophenone 

Relevant academic research and scientific papers

B(C6F5)3-catalyzed Markovnikov addition of indoles to aryl alkynes: An approach toward bis(indolyl)alkanes

The first example of the metal-and solvent-free B(C6F5)3-catalyzed Markovnikov addition of indoles to aryl alkynes was disclosed. Both N-H and N-protected indoles were tolerated, leading to a wide spectrum of versatile bis

Condensation reactions of indole with acetophenones affording mixtures of 3,3-(1-phenylethane-1,1-diyl)bis(1H-indoles) and 1,2,3,4-tetrahydro-3-(1H-indol-3-yl)-1-methyl-1,3-diphenylcyclopent[b]indoles

Condensation of indole 1a with eight acetophenones 8a–h in ethanolic HCl afforded the corresponding mixtures of condensation products: 3,3-(1-phenylethane-1,1-diyl)bis(1H-indoles) 11a–h (2:1 condensation of indole:acetophenone, –H2O) and diaste

FeCl3-catalyzed self-condensation of enamides for the synthesis of enamido-substituted nitrogen-containing quaternary carbon centers

The FeCl3-catalyzed self-condensation of enamides offers a new strategy for the synthesis of enamido-substituted nitrogen-containing quaternary carbon centers, which are attractive structures in organic chemistry. The reaction affords nitrogen-containing quaternary carbon centers in good yields under mild reaction conditions. The catalytic system was also employed in the condensation of enamides with indoles for the synthesis of bis-indoles. The FeCl3-catalyzed self-condensation of enamides for the synthesis of enamido-substituted nitrogen-containing quaternary carbon centers has been developed. The catalytic system was also employed in the condensation of enamides with indoles for the synthesis of bis-indoles. Copyright

Decarboxylative Addition of Propiolic Acids with Indoles to Synthesize Bis(indolyl)methane Derivatives with a Pd(II)/LA Catalyst

Exploring new protocols for efficient organic synthesis is crucial for pharmaceutical developments. The present work introduces a Pd(II)/LA-catalyzed (LA: Lewis acid) decarboxylative addition reaction for the synthesis of bis(indolyl)methane derivatives. The presence of Lewis acid such as Sc(OTf)3 triggered Pd(II)-catalyzed decarboxylative addition of propiolic acids with indoles to offer the bis(indolyl)methane derivatives in moderate to good yields, whereas neither Pd(II) nor Lewis acid alone was active for this synthesis. The catalytic efficiency of Pd(OAc)2 was highly dependent on the Lewis acidity of the added Lewis acid, that is, a stronger Lewis acid provided a higher yield of the bis(indolyl)methane derivatives. Meanwhile, this Pd(II)/LA-catalyzed decarboxylative addition reaction showed good tolerance toward versatile electron-rich or-deficient substituents on the indole skeleton and on the benzyl ring of propiolic acids. The studies on the in situ 1H NMR kinetics of this Pd(II)/Sc(III) catalysis disclosed the formation of a transient vinyl-Pd(II)/Sc(III) intermediate generated by the pyrrole addition to the alkynyl-Pd(II)/Sc(III) species after decarboxylation, which was scarcely observed before.

Halogen bond-catalyzed friedel-crafts alkylation of indole with ketones and aldehydes for the synthesis of symmetrical 3,3’-diindolylmethanes using simple halogen donor catalyst

The Friedel-Crafts alkylation of indole with ketones and aldehydes had been developed to prepare 3,3’-diindolylmethanes using iodine or NCS as catalysts. Two mild and efficient catalysis systems were provided for the activation of carbonyl compounds and i

Indium(iii) catalyzed reactions of vinyl azides and indoles

Indium trichloride catalyzes the reaction of vinyl azides with unfunctionalized indoles to give vinyl indoles. This is the first example of displacement of the azide group by a carbon nucleophile while preserving the vinyl function. The protocol employs very mild reaction conditions and offers excellent yields of diverse 3-vinyl indoles. It is amenable to gram scale. Access to a library of 3,3′-bis(indolyl)methanes through condensation of vinyl azides with 2 equiv of an indole is demonstrated.

A practical synthesis of bis(indolyl)methanes catalyzed by BF 3·Et2O

Practical BF3·Et2O catalyzed reactions between indoles and a series of carbonyl compounds at room temperature are described, which afford bis(indolyl)methanes with isolated yields up to 96%.

Succinimide-N-sulfonic acid catalyzed synthesis of bis(indolyl)methane and coumarin derivatives under mild conditions

A mild and simple procedure is described for the synthesis of bis(indolyl)methane and coumarin derivatives using succinimide-N-sulfonic acid as an efficient, cheap, and reusable catalyst under mild conditions.

Synthesis of diindolylmethanes (DIMs) catalyzed by silicotungstic acid by grinding method

The synthesis of diindolylmethanes (DIMs) via the condensation of indole and aromatic aldehydes catalyzed by silicotungstic acid was carried out in 68%~98% yields at room temperature within 1~5 min by grinding. This method provides several advantages such