62167-04-8

Upstream product

• 698-02-2 N,N-dimethyl-o-iodoaniline 
• 768-60-5 4-methoxyphenylacetylen 
• 219605-51-3 N,N-dimethyl-2-((trimethylsilyl)ethynyl)benzenamine 
• 696-62-8 para-iodoanisole 
• 219605-52-4 2′-N,N-dimethylaminophenylacetylene 

Downstream Products

• 1196785-91-7 ethyl 4-[2-(4-methoxyphenyl)-1-methylindol-3-yl]benzoate 
• 1198116-18-5 3-fluoro-11-methyl-5,6-diphenyl-11H-benzo[a]carbazole 
• 1198116-16-3 3-methoxy-11-methyl-5,6-diphenyl-11H-benzo[a]carbazole 
• 938375-09-8 2-(4-methoxyphenyl)-1-methyl-1H-indole-3-carbonitrile 
• 136672-24-7 (4-methoxyphenyl)(1-methyl-3-indolyl)methane 
• 6910-85-6 1-methyl-2-(4-methoxyphenyl)-3-phenyl-1H-indole 
• 61843-43-4 N-methyl-2-(4-methoxyphenyl)indole 
• 1185743-97-8 2-(4-methoxyphenyl)-1-methyl-3-(p-tolylsulfenyl)indole 
• 1618087-08-3 11-(4-methoxyphenyl)-5-methyl-6-phenyl-5H-indeno[1,2-c]quinoline 
• 1516898-82-0 2-(4-methoxyphenyl)-1methyl-3-(trifluoromethylthio)-1H-indole 
• 98647-17-7 (4-methoxyphenyl)(1-methyl-1H-indol-3-yl)methanone 
• 1445138-72-6 C₂₅H₂₁NO 
• 1445138-71-5 C₂₅H₂₁N 
• 1185743-96-7 2-(4-methoxyphenyl)-1-methyl-3-(phenylsulfenyl)indole 

Relevant academic research and scientific papers

Au-promoted Pd-catalyzed arylative cyclization of N,N-dimethyl-o-alkynylaniline with aryl iodides: Access to 2,3-diaryl indoles and mechanistic insight

We have developed a Au-promoted Pd-catalyzed cyclization/cross-coupling of N,N-dimethyl-o-alkynylaniline with aryl iododes to synthesize 2,3-diarylindoles under mild and base-free conditions. A related vinyl-Au species has been isolated through Au-promoted cyclization of N,N-dimethyl-o-alkynylaniline and structurally characterized. Further study on its reactivity suggests the vinyl-Au species might be out of catalytic cycle, and PhPd(OTf)(PPh3)2 is probably the reaction intermediate.

Intramolecular Addition of a Dimethylamino C(sp 3)-H Bond across C-C Triple Bonds Using IrCl(DTBM-SEGPHOS)(ethylene) Catalyst: Synthesis of Indoles from 2-Alkynyl- N -methylanilines

Intramolecular addition of a C(sp 3)-H bond of the dimethylamino group across the C-C triple bond in 2-alkynyl- N, N -dimethylanilines is effectively catalyzed by a new iridium complex, IrCl(DTBM-SEGPHOS)(C 2H 4), in mesitylene at 150 °C. The intramolecular C(sp 3)-H addition is followed by double-bond isomerization to afford 3-substituted indoles in good to high yields.

Synthesis of: N -alkyl-3-sulfonylindoles and N -alkyl-3-sulfanylindoles by cascade annulation of 2-alkynyl- N, N -dialkylanilines

An efficient and metal-free approach to N-alkyl-3-sulfonylindoles and N-alkyl-3-sulfanylindoles from 2-alkynyl-N,N-dialkylanilines has been developed. In the presence of iodine and tert-butylhydroperoxide (TBHP), a variety of 2-alkynyl-N,N-dialkylanilines underwent a cascade radical annulation to yield 3-arylsulfonylindoles. In contrast, 3-arylsulfanylindoles were conveniently prepared by iodine mediated electrophilic annulation reactions. The present protocol uses the economical and environmentally friendly I2-TBHP or I2 system, and potentially bioactive N-alkyl-3-sulfonylindoles and N-alkyl-3-sulfanylindoles with various functional groups were successfully synthesized in moderate to good yields.

Pd/C-catalyzed cyclizative cross-coupling of two ortho-alkynylanilines under aerobic conditions: Synthesis of 2,3′-bisindoles

Abstract A palladium-catalyzed cyclizative cross-coupling of two o-alkynylanilines to 2,3′-bisindoles under aerobic oxidative conditions was developed. Mechanistic studies suggested that the two catalytic cycles, namely the formation of 3-alkynylindoles 8

CuBr-promoted tandem cyclization/trifluoromethylation of 2-alkynylanilines: Efficient synthesis of 3-trifluoromethylindoles

A new efficient strategy for the synthesis of 3-trifluoromethyl-indoles was developed through tandem cyclization/ trifluoromethylation of 2-alkynylanilines and Umemoto’s reagent under effect of CuBr. The reaction features the use of cheap copper salt, mil

Palladium-catalyzed coupling of ortho-alkynylanilines with terminal alkynes under aerobic conditions: Efficient synthesis of 2,3-disubstituted 3-alkynylindoles

Two nucleophiles, one triple bond: Under aerobic conditions, palladium-catalyzed direct coupling of o-alkynylanilines and terminal alkynes took place smoothly to afford the 2,3-disubstituted 3-alkynylindoles 3 in good to excellent yields. The intermediate A was characterized and a retro-aminopalladation of B was observed for the first time. Copyright

Palladium(II)-catalyzed tandem cyclization/C-H functionalization of alkynes for the synthesis of functionalized indoles

A palladium-catalyzed tandem cyclization/C-H functionalization of two alkynes was accomplished to construct a series of polycyclic functionalized indoles. A range of internal alkynes bearing synthetically useful functional groups were tolerated. A good regioselectivity was observed when alkyl-substituted alkynes were introduced into the reaction system, and a single product was obtained. Molecular oxygen was used as the terminal oxidant in the approach, rendering the reaction more sustainable.

Synthesis of 3-sulfenyl- and 3-selenylindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal alkynes, followed by n-Bu4NI-induced electrophilic cyclization

(Chemical Equation Presented) 3-Sulfenyl- and 3-selenylindoles are readily synthesized by a two-step process involving the palladium/copper-catalyzed crossing coupling of N,N-dialkyl-ortho-iodoanilines and terminal alkynes and subsequent electrophilic cyclization of the resulting N,N-dialkyl-ortho-(1- alkynyl)anilines with arylsulfenyl chlorides or arylselenyl chlorides. The presence of a stoichiometric amount of n-Bu4NI is crucial to the success of the electrophilic cyclization. A variety of 3-sulfenyl- and 3-selenylindole derivatives bearing alkyl, vinylic, aryl, and heteroaryl substituents have been prepared in good to excellent yields (up to 99%). By employing N,N-dibenzyl-ortho-iodoanilines, a 3-sulfenyl-N-H-indole has been successfully prepared. In addition, 3-sulfonyl- and 3-sulfinylindoles have also been successfully prepared by facile oxidation of the corresponding 3-sulfenylindoles.

An efficient, microwave-assisted, one-pot synthesis of indoles under Sonogashira conditions

A microwave-assisted, one-pot, three-component coupling reaction for the synthesis of indoles has been developed. The reaction is carried out in two steps under standard Sonogashira coupling conditions from an N-substituted/N,N-disubstituted 2-iodoaniline and a terminal alkyne, followed by the addition of acetonitrile and an aryl iodide. A variety of polysubstituted indoles have been prepared in moderate to excellent yields using the present method.