2415-33-0Relevant articles and documents
Palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with 1-bromoalkynes. An approach to 2-substituted 3-alkynylindoles and 2-substituted 3-acylindoles
Arcadi, Antonio,Cacchi, Sandro,Fabrizi, Giancarlo,Marinelli, Fabio,Parisi, Luca M.
, p. 6213 - 6217 (2005)
The palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with 1-bromoalkynes affords free N-H 2-substituted 3-alkynylindoles in satisfactory to high yield. 2-Substituted 3-alkynylindoles revealed useful intermediates for the regioselective synthesis of 2-substituted 3-acylindoles. The latter can be prepared from o-alkynyltrifluoroacetanilides and 1-bromoalkynes via a one-pot cyclization-hydration protocol, omitting the isolation of 2-substituted 3-alkynylindoles.
Carbocatalytic Oxidative Dehydrogenative Couplings of (Hetero)Aryls by Oxidized Multi-Walled Carbon Nanotubes in Liquid Phase
Wirtanen, Tom,Aikonen, Santeri,Muuronen, Mikko,Melchionna, Michele,Kemell, Marianna,Davodi, Fatemeh,Kallio, Tanja,Hu, Tao,Helaja, Juho
supporting information, p. 12288 - 12293 (2019/09/06)
HNO3-oxidized carbon nanotubes catalyze oxidative dehydrogenative (ODH) carbon–carbon bond formation between electron-rich (hetero)aryls with O2 as a terminal oxidant. The recyclable carbocatalytic method provides a convenient and an operationally easy synthetic protocol for accessing various benzofused homodimers, biaryls, triphenylenes, and related benzofused heteroaryls that are highly useful frameworks for material chemistry applications. Carbonyls/quinones are the catalytically active site of the carbocatalyst as indicated by model compounds and titration experiments. Further investigations of the reaction mechanism with a combination of experimental and DFT methods support the competing nature of acid-catalyzed and radical cationic ODHs, and indicate that both mechanisms operate with the current material.
2-Substituted 3-arylindoles through palladium-catalyzed arylative cyclization of 2-alkynyltrifluoroacetanilides with arylboronic acids under oxidative conditions
Arcadi, Antonio,Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Iazzetti, Antonia,Marinelli, Fabio
supporting information, p. 545 - 548 (2013/02/26)
Free NH 2-substituted 3-arylindoles have been prepared usually in good to high yields through the palladium-catalyzed reaction of readily available 2-alkynyltrifluoroacetanilides with arylboronic acids under oxidative conditions. The reaction tolerates a variety of useful functional groups both in the arylboronic acid and in the alkyne, including chloro, formyl, and ester groups.