多取代1,3 - 二烯和丙二烯的可调构建：一种1,4 - 钯迁移/卡宾插入串联反应
Tunable Construction of Multisubstituted 1,3-Dienes and Allenes a 1,4-Palladium Migration/Carbene Insertion Cascade.
作者信息
Lin Jie, Huang Zilong, Ma Juan, Xu Bao-Hua, Zhou Yong-Gui, Yu Zhengkun
机构信息
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. China.
University of Chinese Academy of Sciences, Beijing 100049, P. R. China.
出版信息
J Org Chem. 2022 Sep 16;87(18):12019-12035. doi: 10.1021/acs.joc.2c01019. Epub 2022 Sep 2.
Efficient palladium-catalyzed vinylic C-H alkenylation and allenylation of -disubstituted ethylenes with -tosylhydrazones of aryl alkyl and diaryl ketones were achieved to access trisubstituted 1,3-dienes and tetrasubstituted allenes, respectively. An aryl to vinyl 1,4-palladium migration/carbene insertion/β-hydride elimination sequence proceeded to switch the chemo- and regioselectivities to give structurally diverse products. Use of 2-FCHOH additive enables enhancement of the reaction efficiency through accelerating the key 1,4-palladium migration process.
实现了钯催化的芳基烷基和二芳基酮的对甲苯磺酰腙与二取代乙烯的高效乙烯基C-H烯基化和烯丙基化反应，分别得到三取代的1,3-二烯和四取代的丙二烯。通过芳基到乙烯基的1,4-钯迁移/卡宾插入/β-氢消除序列，实现了化学和区域选择性的切换，从而得到结构多样的产物。使用2-FCHOH添加剂可通过加速关键的1,4-钯迁移过程来提高反应效率。
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