4757-69-1Relevant articles and documents
A palladium-catalyzed Barluenga cross-coupling – Reductive cyclization sequence to substituted indoles
Rahman, S. M. Ashikur,S?derberg, Bj?rn C. G.
, (2021/07/20)
A short and flexible synthesis of substituted indoles employing two palladium-catalyzed reactions, a Barluenga cross-coupling of p-tosylhydrazones with 2-nitroarylhalides followed by a palladium–catalyzed, carbon monoxide–mediated reductive cyclization has been developed. A one-pot, two-step methodology was further developed, eliminating isolation and purification of the cross-coupling product. This was accomplished by utilizing the initially added 0.025 equivalents of bis(triphenylphosphine)palladium dichloride, thus serving a dual role in the cross-coupling and the reductive cyclization. It was found that addition of 1,3-bis(diphenylphosphino)propane and carbon monoxide after completion of the Barluenga reaction afforded, in most cases, significantly better overall yields.
Modular counter-Fischer?indole synthesis through radical-enolate coupling
Chung, Hyunho,Kim, Jeongyun,Gonzalez-Montiel, Gisela A.,Cheong, Paul Ha-Yeon,Lee, Hong Geun
supporting information, p. 1096 - 1102 (2021/01/26)
A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.
Regiospecificity in Ligand-Free Pd-Catalyzed C-H Arylation of Indoles: LiHMDS as Base and Transient Directing Group
Camp, Clément,Canivet, Jér?me,Clot, Eric,Demarcy, Clément,Mohr, Yorck,Quadrelli, Elsje Alessandra,Renom-Carrasco, Marc,Thieuleux, Chloé,Wisser, Florian M.
, p. 2713 - 2719 (2020/03/11)
A highly efficient catalyst-base pair for the C-H arylation of free (NH)-indoles in the C-3 position is reported. Ligand-free palladium acetate coupled with lithium hexamethyldisilazide (LiHMDS) catalyzed the regiospecific, i.e. 100% regioselective, C-3 a
