We disclose a novel Pd-catalyzed
assembly of fluoren-9-ones by
merging of C–H activation and difluorocarbene transfer. ClCF2COONa served as a difluorocarbene precursor to be harnessed
as a carbonyl source in this transformation. The current protocol
enables us to afford fluoren-9-ones in high yields with excellent
functional group compatibility, which also represents the first example
of using difluorocarbene as a coupling partner in transition-metal-catalyzed
C–H activation.
Two L-phenylalanine based compounds containing different alkyl chains (designated as 1 and 2) were synthesized and their gelation properties were examined. Gelation test showed that 2 with longer hydrocarbon chain functioned as better gelator than 1 with shorter hydrocarbon chain because of its lower critical gelation concentration (CGC) values in the most of solvents tested. The morphologies of some xerogels were investigated by scanning electron microscope (SEM) and the molecular packing model of LMOGs in the organogel was studied by X-ray diffraction analysis. FTIR analysis revealed that the van der Waals interaction between the alkyl chains and the intermolecular hydrogen bonding between the amide groups and the carboxy groups should be an important driving force for the formation of the organogels. Interestingly, two compounds also showed phase-selective gelation of the solvents from their mixtures with water.
The Pd(0)-catalyzed tandem intermolecular syn-carbopalladation/asymmetric C–H alkenylation reaction of N-ferrocenyl propiolamides with aryl iodides has been realized, generating planar chiral ferrocene[1,2-d] pyrrolinones in good yields.
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