Palladium-catalyzed cyclocarbonylation-decarboxylation of diethyl(2-iodoaryl)malonates with vinyl ketones affording functionalized enolic 2-acyl-3,4-dihydronaphthalenones.
A wide variety of enolic tautomers of functionalized 2-acyl-3,4-dihydronaphthalen-1(2H)-ones were obtained in moderate to excellent yields by the palladium-catalyzed cyclocarbonylation-decarboxylation of diethyl(2-iodoaryl)malonates with vinyl ketones and carbon monoxide. The reaction may proceed via the formation of a keto-diester, followed by oxidative addition, CO insertion, intramolecular cyclization, and decarboxylation to give the enolic substituted 2-acyldihydronaphthalenones.
Zheng
Zhaoyan
Z
Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada.
Alper
Howard
H
D002248:Carbon Monoxide / Q000737:chemistry; D002384:Catalysis; D003653:Decarboxylation; D007659:Ketones / Q000737:chemistry*; D008314:Malonates / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
D007659:Ketones; D008314:Malonates; D010165:Palladium; D002248:Carbon Monoxide