Palladium-catalysed aryl/monofluoroalkylation of allenamides: access to fluoroalkyl indoles and isoquinolones

Abstract

A palladium catalysed construction of fluoroalkyl indoles and isoquinolones through aryl/monofluoroalkylation of allenamides has been developed. Monofluoromethyl-substituted heterocycles could be accessed under mild conditions with broad functional groups tolerance. In...

Synthesis of Substituted 1,2-Dihydroisoquinolines by Palladium-Catalyzed Cascade Cyclization–Coupling of Trisubstituted Allenamides with Arylboronic Acids

“…The reaction was initiated with the oxidative addition of the aryl bromide moiety of the allenamide 2 to palladium, generating arylpalladium intermediate A [ 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 ]. This was followed by an intramolecular allene insertion process ( B ) to generate the π-allyl-palladium intermediate C [ 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 ]. Then, ligand exchange of palladium complex C with hydroxide ion occurred, forming hydroxypalladium species D [ 39 ].…”

“…Allenamides are powerful and versatile synthetic building blocks in organic synthesis, extensively utilized as reaction substrates to produce a variety of synthetically useful organic molecules [ 23 , 24 ]. Among them, palladium-catalyzed cascade cyclization of ortho-haloaryl-substituted allenamides provides efficient approaches for the synthesis of N -heterocyclic compounds ( Scheme 1 , eq 1) [ 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 ]. The key intermediate in this strategy is the π-allylpalladium species, which is generated by an oxidative addition and allene insertion sequence.…”