Cooperative Trifluoromethyl Group and Catalyst-Enabled Regioselective 3,4-Functionalization of Unsymmetric β-CF3-1,3-enynes via C–H Bond Activation
Yongshun Wen , Yun Liao , Mei Xiao , Jin Zhu , Li-Juan Tang , Yingtong Zong , Wenjun Luo , Zhengwang Chen , Daohong Yu
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (19) : 2512 -2518.
Cooperative Trifluoromethyl Group and Catalyst-Enabled Regioselective 3,4-Functionalization of Unsymmetric β-CF3-1,3-enynes via C–H Bond Activation
1-Isoquinolin-1(2H)-one skeleton exists widely in natural products, pharmaceuticals and materials. We disclose here a fluorine effect and catalyst cooperatively induced regioselective or regiospecific 3,4-functionalization of unsymmetric 2-CF3-1,3-enynes. The presence of trifluoromethyl group is determinable for the regioselectivity. When the CF3 group was replaced with the methyl or amide group, the regioselectivity decreased to a ratio of 1.3 : 1 or 1 : 1.7, respectively. For alkyl substituted β-CF3-1,3-enynes, a regiospecificity was obtained. This strategy features excellent regioselectivity, broad substrate scope and high functional group tolerance. Mechanistic studies showed that C–H bond activation is the rate-limiting step.
C–H activation / Unsymmetric internal alkyneβ-CF3-1,3-enyne / Cooperative CF3 group and catalyst control strategy / 1-Isoquinolin-1(2H)-one / Transition metal catalyzed / Synthetic methods / CF3-vinyl isoquinolin-1-one / Alkynes / 3d transition metals / Homogeneous catalysis
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH.
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