Palladium-Catalyzed C(sp3)-H Oxygenation via Electrochemical Oxidation

被引:297
作者
Yang, Qi-Liang [1 ,2 ,3 ]
Li, Yi-Qian [1 ]
Ma, Cong [1 ]
Fang, Ping [1 ]
Zhang, Xiu-Jie [1 ]
Mei, Tian-Sheng [1 ]
机构
[1] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai Inst Organ Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China
[2] East China Univ Sci & Technol, Key Lab Adv Mat, Sch Chem & Mol Engn, Meilong Rd 130, Shanghai 200237, Peoples R China
[3] East China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, Meilong Rd 130, Shanghai 200237, Peoples R China
关键词
C-H BONDS; FORMING REDUCTIVE ELIMINATION; O-ALLYL ETHERS; C(SP(2))-H BONDS; DIRECTING-GROUP; UNACTIVATED C(SP(3))-H; COUPLING REACTIONS; METHYL-GROUPS; CARBON BONDS; FUNCTIONALIZATION;
D O I
10.1021/jacs.7b01232
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Palladium-catalyzed C-H activation/C-O bond-forming reactions have emerged as attractive tools for organic synthesis. Typically, these reactions require strong chemical oxidants, which convert organopalladium(II) intermediates into the Pd-III or Pd-IV oxidation state to promote otherwise challenging C-O reductive elimination. However, previously reported oxidants possess significant disadvantages, including poor atom economy, high cost, and the formation of undesired byproducts. To overcome these issues, we report an electrochemical strategy that takes advantage of anodic oxidation of Pd-II induce selective C-reductive elimination with a variety of oxyanion coupling partners.
引用
收藏
页码:3293 / 3298
页数:6
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