6774-26-1Relevant academic research and scientific papers
Irradiation-Induced Palladium-Catalyzed Direct C-H Alkylation of Heteroarenes with Tertiary and Secondary Alkyl Bromides
Wang, Guang-Zu,Shang, Rui,Fu, Yao
, p. 2908 - 2914 (2018)
A palladium catalyst in combination with two types of phosphine ligands efficiently catalyzes direct C-H alkylation of heteroarenes with secondary and tertiary alkyl bromides under irradiation conditions. Irradiation of blue light-emitting diodes (blue LEDs) effectively excites phosphine-ligated palladium catalyst to facilitate oxidative addition with alkyl bromides, and also excites the alkylpalladium species to enable the generation of alkyl radicals to react with heteroarenes.
Cyclopenta[b]annulation of Heteroarenes by Organocatalytic γ′[C(sp3)?H] Functionalization of Ynones
Raghu, Moluguri,Grover, Jagdeep,Ramasastry
supporting information, p. 18316 - 18321 (2016/12/16)
A new approach for the cyclopenta[b]annulation of heteroarenes through metal-free and directing-group-free γ′[C(sp3)?H] functionalization and intramolecular hydroalkylation of ynones has been developed. In an unprecedented event, nucleophilic addition of an organophosphine to the designed ynones triggers γ′[C(sp3)?H] functionalization, leading to the formation of heteroaryl-based ortho-quinodimethane (oQDM) intermediates that undergo carbocyclization to provide cyclopentannulated heteroarenes in good yields and excellent stereoselectivities. Deuterium-labeling experiments substantiated the proposed reaction mechanism as well as the speculated epimerization.
A general palladium-catalyzed method for alkylation of heteroarenes using secondary and tertiary alkyl halides
Wu, Xiaojin,See, Jessica Wei Ting,Xu, Kai,Hirao, Hajime,Roger, Julien,Hierso, Jean-Cyrille,Zhou, Jianrong
supporting information, p. 13573 - 13577 (2015/01/09)
A general alkylation of heterocycles using a simple palladium catalyst is reported. Most classes of heterocycles, including indoles and pyridines, efficiently coupled with unactivated secondary and tertiary alkyl halides. An alkyl radical addition to neutral heteroarenes is most likely involved.
