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

TY - JOUR

T1 - Pd-catalysed intramolecular regioselective arylation of 2-pyrones, pyridones, coumarins and quinolones by C-H bond functionalization

AU - Nolan, M.-T.

AU - Bray, J.T.W.

AU - Eccles, K.

AU - Cheung, M.S.

AU - Lin, Z.

AU - Lawrence, S.E.

AU - Whitwood, A.C.

AU - Fairlamb, I.J.S.

AU - McGlacken, G.P.

PY - 2014/10/7

Y1 - 2014/10/7

N2 - The intramolecular arylation of 2-pyrones, 2-pyridones, coumarins and quinolones is reported using Pd 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.

AB - The intramolecular arylation of 2-pyrones, 2-pyridones, coumarins and quinolones is reported using Pd 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.

KW - Palladium

KW - Cross-Coupling

KW - Catalysis

KW - Organic Chemistry

KW - Synthetic Chemistry

KW - MECHANISM

UR - http://www.scopus.com/inward/record.url?scp=84900115168&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2014.04.029

DO - 10.1016/j.tet.2014.04.029

M3 - Article

SN - 0040-4020

VL - 70

SP - 7120

EP - 7127

JO - Tetrahedron

JF - Tetrahedron

IS - 40

ER -