Cu(I)-Catalyzed C–H Alkenylation of Tertiary C(sp³)–H Bonds of 3-Aryl Benzofuran-2(3H)-ones to Give Z- and E-Styrene Containing Quaternary Carbon Centers with 99/1 Regioselectivity
2022
Tong, Zhou | Peng, Xinju | Peng, Lifen | Deng, Wei | Wang, Zhiqing | Lu, Hao | Yang, Weijun | Yin, Shuang-Feng | Kambe, Nobuaki | Qiu, Renhua
The synthesis of isomerically pure olefins containing all-carbon quaternary centers is a challenging issue. Herein, we developed an efficient protocol for the synthesis of (Z)-olefins (27 examples, yield up to 97%, Z/E up to 99/1) and (E)-olefins (16 examples, yield up to 94%, E/Z up to 99/1) containing all-carbon quaternary centers. This protocol is adopted for the copper-catalyzed regioselective C–H alkenylation of the tertiary C(sp³)–H bond of 3-aryl benzofuran-2(3H)-ones with alkyne and alkenes. A diverse range of functional groups in the substrates is well-tolerated, such as F, Cl, Br, Me, OMe, ester, CF₃, etc. A gram scale experiment was performed in good yield, and the radical mechanisms are also proposed based on the control experiments.
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