Nickel-catalyzed reductive cleavage of aryl-oxygen bonds in alkoxy- and pivaloxyarenes using hydrosilanes as a mild reducing agent

被引:159
作者
Tobisu, Mamoru [1 ]
Yamakawa, Ken [2 ]
Shimasaki, Toshiaki [1 ]
Chatani, Naoto [2 ]
机构
[1] Osaka Univ, Grad Sch Engn, Suita, Osaka 5650871, Japan
[2] Osaka Univ, Dept Appl Chem, Fac Engn, Suita, Osaka 5650871, Japan
关键词
CROSS-COUPLING REACTIONS; CARBON-CARBON BONDS; BIOLOGICAL EVALUATION; ETHERS; ACTIVATION; FUNCTIONALIZATION; INHIBITORS; AMINATION; MECHANISM; ARYLATION;
D O I
10.1039/c0cc05169a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A nickel-catalyzed reductive deoxygenation of aryl alkyl ethers and aryl pivalates has been developed. Hydrosilanes serve as a mild reducing agent. The present protocol allows the use of a pivalate group as a robust and traceless steering group in arene functionalization reactions.
引用
收藏
页码:2946 / 2948
页数:3
相关论文
共 36 条
  • [11] HARTUNG WH, 1953, ORG REACTIONS, V7, P263
  • [12] Use of Protein Tyrosine Phosphatase Inhibitors as Promising Targeted Therapeutic Drugs
    Heneberg, P.
    [J]. CURRENT MEDICINAL CHEMISTRY, 2009, 16 (06) : 706 - 733
  • [13] Ruthenium-catalyzed functionalization of aryl carbon-oxygen bonds in aromatic ethers with organoboron compounds
    Kakiuchi, F
    Usui, M
    Ueno, S
    Chatani, N
    Murai, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (09) : 2706 - 2707
  • [14] Interval recursive least-squares filtering with applications to video target tracking
    Li, Baohua
    Li, Changchun
    Si, Jennie
    Abousleman, Glen P.
    [J]. OPTICAL ENGINEERING, 2008, 47 (10)
  • [15] Cross-Coupling of Alkenyl/Aryl Carboxylates with Grignard Reagent via Fe-Catalyzed C-O Bond Activation
    Li, Bi-Jie
    Xu, Li
    Wu, Zhen-Hua
    Guan, Bing-Tao
    Sun, Chang-Liang
    Wang, Bi-Qin
    Shi, Zhang-Jie
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (41) : 14656 - +
  • [16] Mechanism of Ni-Catalyzed Selective C-O Bond Activation in Cross-Coupling of Aryl Esters
    Li, Zhe
    Zhang, Song-Lin
    Fu, Yao
    Guo, Qing-Xiang
    Liu, Lei
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (25) : 8815 - 8823
  • [17] Mechanistic study of a Pd/C-catalyzed reduction of aryl sulfonates using the Mg-MeOH-NH4OAc system
    Mori, Akinori
    Mizusaki, Tomoteru
    Ikawa, Takashi
    Maegawa, Tomohiro
    Monguchi, Yasunari
    Sajiki, Hironao
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (05) : 1432 - 1441
  • [18] Lewis base catalyzed asymmetric reactions involving hypervalent silicate intermediates
    Orito, Y
    Nakajima, M
    [J]. SYNTHESIS-STUTTGART, 2006, (09): : 1391 - 1401
  • [19] sp3 C-H bond arylation directed by amidine protecting group:: α-arylation of pyrrolidines and piperidines
    Pastine, Stefan J.
    Gribkov, Denis V.
    Sames, Dalibor
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (44) : 14220 - 14221
  • [20] Cross-Coupling Reactions of Aryl Pivalates with Boronic Acids
    Quasdorf, Kyle W.
    Tian, Xia
    Garg, Neil K.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (44) : 14422 - +