A versatile copper-catalyzed coupling reaction of pyridin-2(1H)-ones with aryl halides

Copper‐Catalyzed Double Intramolecular Ullmann Coupling for the Synthesis of Diastereomerically and Enantiomerically Pure 4b,9b‐Dihydrobenzofuro[3,2‐b]benzofurans

“…Since the 8‐hydroxyquinoline ligand can easily be exchanged for other ligands,19b these complexes, which are usually prepared in situ, are potential catalysts. In addition to the already mentioned O ‐arylations, a variety of other reactions, including C ‐vinylations of arylboronic acids,19c N ‐arylations of pyridine‐2(1 H )‐ones,19d pyridazones19e and imidazoles,19f and the synthesis of methyl benzoates from benzyl alcohol and tert ‐butyl hydroperoxide,19g can be catalyzed by Cu II oxinate or by using a copper source in the presence of 8‐hydroxyquinoline as a ligand. With Cu II oxinate (10 mol‐%) and K 3 PO 4 (4 equiv.)…”

Divergent synthesis of arylated pyridin-2(1H)-one derivatives via metal-catalysed cross-coupling processes

“…28,44 To explore this reaction, pyridone derivative 8 was reacted with 11 (Scheme 2). After isolation of the N-heteroarylated product 12a vide infra, a comparison with the crude 1 H NMR spectrum and GCeMS traces confirmed that 12a was the major product.…”

“…Whilst keeping the same base (Cs 2 CO 3 ), the solvent was changed to dioxane, 8-hydroxyquinoline (8-HQ) was employed as the ligand and PEG was added as a solideliquid transfer catalyst. 45 However, despite 8-HQ being previously used to N-arylated pyridones 44 and pyridazinones, 27 these conditions resulted in a low conversion and a reduced ratio …”

“…On the basis of these results it is more likely that the steric effect of a 6-fluoro substituent hampers the arylation of 36, as well as the electron withdrawing effect of the fluorine atom resulting in a reduced nucleophilicity. 44 An attempt to arylate 36 by copper-catalysed coupling with phenylboronic acid (DCM, room temperature, 48 h) 24 gave an intractable reaction mixture. Table 3.…”

Coupling Reactions of α-Bromocarboxylate with Non-Aromatic N-Heterocycles

“…Several reviews describing recent progress of copper-mediated coupling reactions for C-N bond formation have been published [8,9,10] and nucleophilic substitutions using copper(I) catalysts were described in other papers where copper(I) oxide [11,12], sulfide [13,14], iodide [15,16] or other copper(I) derivatives were used [17]. Contrary to the above referred articles dealing mostly with copper-mediated arylation of aromatic or aliphatic amines, coupling of the aliphatic compounds is discussed in this paper.…”