Journal
ORGANOMETALLICS
Volume 36, Issue 17, Pages 3343-3351Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.organomet.7b00478
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Funding
- Science & Engineering Research Board (SERB), New Delhi [SR/S1/IC-58/2012, SR/S2/RJN-49/2011, SR/S1/PC/0060/2010]
- Department of Atomic Energy (DAE)
- CSIR
- DST
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Regioisomers of 3,5-dipheny1-1-(4-(trifluoromethyl)pheny1)1H-pyrazole-based palladacycles (1 and 2) were synthesized by the aromatic C-H bond activation of N/3-aryl ring. The application of these regioisomers as catalysts to enable the formation of a-alkylated ketones or quinolines with alcohols using a hydrogen borrowing process is evaluated. Experimental results reveal that palladacycle 2 is superior over palladacycle 1 to catalyze the reaction under similar reaction conditions. The reaction mechanisms for the palladacycles 1 and 2 catalyzed alpha-alkylation of acetophenone were studied using density functional theoretical (DFT) methods. The DFT studies indicate that palladacycle 2 has an energy barrier lower than that of palladacycle 1 for the alkylation reaction, consistent with the better catalytic activity of palladacycle 2 seen in the experiments. The palladacyde phosphine system was found to tolerate a wide range of functional groups and serves as an efficient protocol for the synthesis of a-alkylated products under solvent-free conditions. In addition, the synthetic protocol was successfully applied to prepare donepezil, a drug for Alzheimer's disease, from simple starting materials.
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