A Pd-catalyzed heteroannulation approach to 2,3-disubstituted furo[3,2-c]coumarins.
The Pd-catalyzed cyclofunctionalization of 3-alkynyl-4-methoxycoumarins with aryl halides resulted in the selective formation of 3-arylfuro[3,2-c]coumarins in lieu of the expected regioisomeric 3-arylfuro[2,3-b]chromones. A mechanism involving the linear to angular rearrangement of a Pd-containing furan intermediate was proposed.
Raffa
Guillaume
G
ICBMS, Institut de Chimie et Biochimie Moléculaire et Supramoléculaire, CNRS UMR 5246, Université Lyon 1, ESCPE Lyon 43, Boulevard du 11 Novembre 1918, 69622 Villeurbanne, France.
Rusch
Marion
M
Balme
Geneviève
G
Monteiro
Nuno
N
D002384:Catalysis; D018360:Crystallography, X-Ray; D011564:Furocoumarins / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D011564:Furocoumarins; D010165:Palladium