Site-Selective Pd-Catalyzed C(sp3)?H Arylation of Heteroaromatic Ketones
A ligand-controlled site-selective C(sp3)?H arylation of heteroaromatic ketones has been developed using Pd catalysis. The reaction occurred selectively at the α- or β-position of the ketone side-chain. The switch from α- to β-arylation was realized by addition of a pyridone ligand. The α-arylation process showed broad scope and high site- and chemoselectivity, whereas the β-arylation was more limited. Mechanistic investigations suggested that α-arylation occurs through C?H activation/oxidative addition/reductive elimination whereas β-arylation involves desaturation and aryl insertion.
Kudashev, Anton,Baudoin, Olivier
supporting information
p. 17688 - 17694
(2021/11/16)
Photoinduced Remote Functionalisations by Iminyl Radical Promoted C?C and C?H Bond Cleavage Cascades
A photoinduced cascade strategy leading to a variety of differentially functionalised nitriles and ketones has been developed. These reactions rely on the oxidative generation of iminyl radicals from simple oximes. Radical transposition by C(sp3)?(sp3) and C(sp3)?H bond cleavage gives access to distal carbon radicals that undergo SH2 functionalisations. These mild, visible-light-mediated procedures can be used for remote fluorination, chlorination, and azidation, and were applied to the modification of bioactive and structurally complex molecules.
Dauncey, Elizabeth M.,Morcillo, Sara P.,Douglas, James J.,Sheikh, Nadeem S.,Leonori, Daniele
supporting information
p. 744 - 748
(2017/12/13)
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