Selectivity control in pd-catalyzed c-h functionalization reactions

Identifier:  TDX:1325

Handle: https://hdl.handle.net/20.500.11797/TDX1325

Authors:  Flores Gaspar, Areli

Abstract:
Benzocyclobutenones are an intriguing four-membered ring ketone. In the present thesis, we have developed a new protocol for selectively preparing benzocyclobutenones through intramolecular acylation of aryl bromides via palladium catalyzed C-H bond functionalization reactions based on rac-BINAP ligand. We also found that a subtle modification on the ligand backbone lead to a new catalytic manifold for preparing configurationally-pure styrene derivatives, when using dcpp (bis-dicyclohexylphosphine ethane) ligand. Additionally, we extended our catalytic intramolecular C-H bond functionalization for preparing benzocyclobutenones or styrenes at will utilizing the more available and less expensive aryl chlorides as substrates. In this particular case, the nature of the N-heterocyclic carbenes (NHC´s) was critical, thus dictating the selectivity pattern.