201735-24-2

Upstream product

• 629-05-0 n-octyne 
• 698-02-2 N,N-dimethyl-o-iodoaniline 

Downstream Products

• 1346164-99-5 2-hexyl-1-methyl-3-(phenylthio)-1H-indole 
• 1448145-40-1 2-hexyl-N-methyl-3-(phenylselenyl)-1H-indole 

Relevant academic research and scientific papers

Palladium(II)-catalyzed cyclizative cross-coupling of ortho-alkynylanilines with ortho-alkynylbenzamides under aerobic conditions

Born to couple: The Pd(OAc)2-catalyzed reaction of o-alkynylanilines (1) with o-alkynylbenzamides (2) affords the cyclizative cross-coupling products 3 in good to excellent yields. Three bonds are created in the formation of two heterocycles tethered by a tetrasubstituted double bond. Mechanistic studies indicate that the reaction is initiated by aminopalladation with subsequent oxypalladation, N-demethylation, and reductive elimination. Copyright

Synthesis of 3-iodoindoles by electrophilic cyclization of N,N-dialkyl-2-(1-alkynyl)anilines

(Equation presented) A wide variety of N-alkyl-3-iodoindoles are readily prepared under very mild reaction conditions by the palladium/copper-catalyzed cross-coupling of N,N-dialkyl-o-iodoanilines and terminal alkynes, followed by electrophilic cyclizatio

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

Synthesis of 3-iodoindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal acetylenes, followed by electrophilic cyclization

3-Iodoindoles have been prepared in excellent yields by coupling terminal acetylenes with N,N-dialkyl-o-iodoanilines in the presence of a Pd/Cu catalyst, followed by an electrophilic cyclization of the resulting N,N-dialkyl-o-(1- alkynyl)anilines using I