Highly Regioselective C-H Alkylation of Alkenes Through an Aryl to Vinyl 1,4-Palladium Migration/C-C Cleavage Cascade
Highly Regioselective C-H Alkylation of Alkenes Through an Aryl to Vinyl 1,4-Palladium Migration/C-C Cleavage Cascade
复制标题
通过芳基到乙烯基 1,4-钯迁移/C-C 裂解级联对烯烃进行高度区域选择性 C-H 烷基化
DOI：
10.1021/acscatal.9b04161
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发表时间：
2019
期刊：
影响因子：
12.9
通讯作者：
Zhengkun Yu
中科院分区：
文献类型：
--
作者：
Quannan Wang;Rongjun Chen;Jiang Lou;Dong H.Zhang;Yong-Gui Zhou;Zhengkun Yu
Palladium-catalyzed C−H alkylation ofgem-disubstituted ethylenes has been efficiently achieved with cyclobutanols as the coupling partners through an aryl to vinyl 1,4-palladium migration/ring-opening C–C cleavage cascade, giving trisubstituted alkenes in high yields. The protocol features good regioselectivity, high yields, broad substrate scopes, and good functional group tolerance. The mechanistic studies implicate that the cross-coupling reaction occurs via oxidative addition, 1,4-palladium migration, ring-opening C–C cleavage, and reductive elimination. DFT calculations have revealed that the high efficiency of the protocol is attributed to the thermodynamically favored 1,4-palladium migration assisted by 2-fluorophenol.
