Palladium-Catalyzed Hydrocarbonylative Cyclization Enabled by Formal Insertion of Aromatic C═N Bonds into Pd-Acyl
Xibing Zhou1, Anrong Chen1, Wei Du2
1Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, Center for Excellence in Molecular Synthesis , University of Science and Technology of China, Chinese Academy of Sciences , Hefei , 230026 , People's Republic of China.
Abstract:
An efficient new formal insertion strategy via combination of reductive elimination and oxidative addition sequence was reported, in which the transient N-acyliminium ions formed via hydrocarbonylation function as key intermediates. This strategy has enabled a novel palladium-catalyzed hydrocarbonylative cyclization of azaarene-tethered alkenes or dienes via sequential insertion of a C═C bond, CO, and a C═N bond into palladium-hydride bonds. This method provides a new and highly efficient synthetic approach to quinolizinones and its derivatives with extended π-conjugated systems, possessing tunable emission wavelengths and good photoluminescence capabilities.
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