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.
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.
Guillaume
G
Raffa
Marion
M
Rusch
Geneviève
G
Balme
Nuno
N
Monteiro
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