Trifluoromethylthio-promoted Nazarov cyclization of α-SCF3-vinyl (hetero)aryl ketones
Sugyeong Kim1, Yu Jin Pyo1, Geon Ryun Park1
1Department of Chemistry and Green-Nano Materials Research Center, Kyungpook National University, Daegu 41566, Republic of Korea. cwcho@knu.ac.kr.
Abstract:
A trifluoromethylthio-promoted Nazarov cyclization of α-SCF3-vinyl (hetero)aryl ketones has been developed using trifluoromethanesulfonic acid in dichloromethane. This efficient protocol affords the corresponding α-SCF3-substituted cyclopentenone-fused polycyclic products in good yields (up to 96%). The bromo-substituted polycyclic products were further utilized in Sonogashira and Suzuki cross-coupling reactions, demonstrating their synthetic versatility. Density functional theory (DFT) calculations revealed that the α-SCF3 substituent lowers the activation barrier, thereby facilitating the cyclization. This strategy provides an efficient route to a novel class of SCF3-substituted polycyclic compounds.
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