PdI2-catalyzed regioselective cyclocarbonylation of 2-allyl phenols to dihydrocoumarins.
A simple, efficient, and regioselective synthesis of 3-methyl-3,4-dihydrocoumarins is reported. The reaction of 2-allyl phenols with synthesis gas was catalyzed by PdI2, and 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane (L1) and 1,3,5,7-tetramethyl-6-tetradecyl-2,4,8-trioxa-6-phosphaadamantane (L2) were effective as ligands, affording good product selectivity in all cases.
Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa , 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada.
Manuel
M
Amézquita-Valencia
Howard
H
Alper
D000218:Adamantane / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D008024:Ligands; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism
C544841:1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane; D003374:Coumarins; D008024:Ligands; D010636:Phenols; D010165:Palladium; D000218:Adamantane