Nolan, MT;Bray, JTW;Eccles, K;Cheung, MS;Lin, ZY;Lawrence, SE;Whitwood, AC;Fairlamb, IJS;McGlacken, GP

2014

October

Tetrahedron

Pd-catalysed intramolecular regioselective arylation of 2-pyrones, pyridones, coumarins and quinolones by C-H bond functionalization

Validated

WOS: 26 ()

METALATION-DEPROTONATION MECHANISM CHOLESTEROL ACYLTRANSFERASE CYCLIZATION REACTION OXIDATIVE ADDITION HECK REACTION ACYL-COA PALLADIUM 4-HYDROXY-2-PYRONES ACETYLCHOLINESTERASE IODOBENZENE

70

7120

7127

The intramolecular arylation of 2-pyrones, 2-pyridones, coumarins and quinolones is reported using Pd-II precatalyst sources without added phosphine ligands. The excellent yields and convenient reagents enables the formation of various analogues containing these moieties, and access to potential biologically active candidates. Stoichiometric studies were carried out to provide an insight into the oxidation addition step. A switch in regioselectivity, together with a hydrodebromination process, was observed in the case of a 3-bromo-2-pyrone. (C) 2014 Elsevier Ltd. All rights reserved.

OXFORD

0040-4020

10.1016/j.tet.2014.04.029