Atmosphere-Controlled Palladium-Catalyzed Divergent Decarboxylative Cyclization of 2-Iodobiphenyls and α-Oxocarboxylic Acids
Liwei Zhou, Mingjie Sun, Fengru Zhou, Guobo Deng, Yuan Yang, Yun Liang
Abstract
A novel palladium-catalyzed divergent decarboxylative cyclization of 2-iodobiphenyls and α-oxocarboxylic acids utilizing the atmosphere as a controlled switch is reported. Under the protection of a nitrogen atmosphere, tribenzotropones are synthesized by a [4 + 3] decarboxylative cyclization. Employing a palladium/O2 system enables a [4 + 2] decarboxylative cyclization to assemble triphenylenes. Notably, preliminary mechanistic studies indicate that the formation of triphenylenes involves a double decarboxylation.
Topics & Concepts
DecarboxylationChemistryPalladiumAtmosphere (unit)CatalysisNitrogenOrganic chemistryCombinatorial chemistryThermodynamicsPhysicsCatalytic C–H Functionalization MethodsSynthesis of Indole DerivativesAxial and Atropisomeric Chirality Synthesis