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

被引:4
|
作者
Tong, Zhou [1 ]
Peng, Xinju [1 ]
Peng, Lifen [1 ,2 ]
Deng, Wei [1 ]
Wang, Zhiqing [1 ,2 ]
Lu, Hao [1 ,2 ]
Yang, Weijun [1 ]
Yin, Shuang-Feng [1 ]
Kambe, Nobuaki [1 ,2 ]
Qiu, Renhua [1 ]
机构
[1] Hunan Univ, Coll Chem & Chem Engn, Adv Catalyt Engn Res Ctr, State Key Lab Chemo Biosensing & Chemometr,Minist, Changsha 410082, Hunan, Peoples R China
[2] Osaka Univ, Inst Sci & Ind Res, Osaka 5670047, Japan
来源
JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 09期
关键词
OLEFIN SYNTHESIS; ALKYL-HALIDES; ARYL; HYDROALKYLATION; SECONDARY; REGIO;
D O I
10.1021/acs.joc.2c00325
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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(sp(3))-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.
引用
收藏
页码:6064 / 6074
页数:11
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