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
来源：
CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 10期
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
  • [1] Ni-Catalyzed Reduction of Inert C-O Bonds: A New Strategy for Using Aryl Ethers as Easily Removable Directing Groups
    Alvarez-Bercedo, Paula
    Martin, Ruben
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (49) : 17352 - 17353
  • [2] Electrophile-induced dearomatizing spirocyclization of N-arylisonicotinamides:: A route to spirocyclic piperidines
    Arnott, Gareth
    Brice, Heloise
    Clayden, Jonathan
    Blaney, Emma
    [J]. ORGANIC LETTERS, 2008, 10 (14) : 3089 - 3092
  • [3] Scalable Total Synthesis and Biological Evaluation of Haouamine A and Its Atropisomer
    Burns, Noah Z.
    Krylova, Irina N.
    Hannoush, Rami N.
    Baran, Phil S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (26) : 9172 - +
  • [4] PALLADIUM-CATALYZED TRIETHYLAMMONIUM FORMATE REDUCTION OF ARYL TRIFLATES - A SELECTIVE METHOD FOR THE DEOXYGENATION OF PHENOLS
    CACCHI, S
    CIATTINI, PG
    MORERA, E
    ORTAR, G
    [J]. TETRAHEDRON LETTERS, 1986, 27 (45) : 5541 - 5544
  • [5] PyDipSi: A General and Easily Modifiable/Traceless Si-Tethered Directing Group for C-H Acyloxylation of Arenes
    Chernyak, Natalia
    Dudnik, Alexander S.
    Huang, Chunhui
    Gevorgyan, Vladimir
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (24) : 8270 - +
  • [6] Synthesis and biological evaluation of chalcones as inhibitors of the voltage-gated potassium channel Kv1.3
    Cianci, Julia
    Baell, Jonathan B.
    Flynn, Bernard L.
    Gable, Robert W.
    Mould, Jorgen A.
    Paul, Dharam
    Harvey, Andrew J.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (06) : 2055 - 2061
  • [7] Nickel-catalyzed cross-coupling of aryl Grignard reagents with aromatic alkyl ethers: An efficient synthesis of unsymmetrical biaryls
    Dankwardt, JW
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (18) : 2428 - 2432
  • [8] Palladium(II)-Catalyzed Regioselective Direct C2 Alkenylation of Indoles and Pyrroles Assisted by the N-(2-Pyridyl)sulfonyl Protecting Group
    Garcia-Rubia, Alfonso
    Gomez Arrayas, Ramon
    Carretero, Juan C.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (35) : 6511 - 6515
  • [9] Biaryl Construction via Ni-Catalyzed C-O Activation of Phenolic Carboxylates
    Guan, Bing-Tao
    Wang, Yang
    Li, Bi-Jie
    Yu, Da-Gang
    Shi, Zhang-Jie
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (44) : 14468 - +
  • [10] Methylation of arenes via Ni-catalyzed aryl C-O/F activation
    Guan, Bing-Tao
    Xiang, Shi-Kai
    Wu, Tao
    Sun, Zuo-Peng
    Wang, Bi-Qin
    Zhao, Ke-Qing
    Shi, Zhang-Jie
    [J]. CHEMICAL COMMUNICATIONS, 2008, (12) : 1437 - 1439
1234