Pd(II)-Catalyzed Synthesis of Benzyl Benzoates via Benzyl C(sp3)-H Activation

被引:3
|
作者
Duanmu, Dandan [1 ]
Leong, Pak-kin [1 ]
Jiang, Qibai [2 ]
Yan, Hong [1 ]
机构
[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China
[2] Jiangsu Yangnong Chem Co Ltd, Yangzhou 225009, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
Pd(II)-catalysis; C-H activation; benzyl benzoates; perester; C-H ACTIVATION; INTRAMOLECULAR ALKANE ARYLATION; CATALYZED ALLYLIC OXIDATION; CROSS-COUPLING REACTIONS; BOND FUNCTIONALIZATION; CARBOXYLIC-ACIDS; CARBONYLATION; ALKYLATION; CLEAVAGE; ESTERS;
D O I
10.6023/cjoc201704040
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient Pd(II)-catalyzed synthesis of benzyl benzoates via direct functionalization of benzyl C(sp(3))-H bonds was developed. The method features a broad substrate scope. This method features high tolerance of functional groups, mild reaction condition, and high chemoselective when there are multiple active C(sp(3))-H bonds. A plausible oxidative coupling mechanism was proposed on the basis of mechanistic studies.
引用
收藏
页码:2669 / 2677
页数:9
相关论文
共 90 条
  • [1] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage
    Ackermann, Lutz
    Vicente, Ruben
    Kapdi, Anant R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9792 - 9826
  • [2] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
    Alberico, Dino
    Scott, Mark E.
    Lautens, Mark
    [J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
  • [3] Copper catalyzed allylic oxidation with peresters
    Andrus, MB
    Lashley, JC
    [J]. TETRAHEDRON, 2002, 58 (05) : 845 - 866
  • [4] Highly enantioselective copper-bisoxazoline-catalyzed allylic oxidation of cyclic olefins with tert-butyl p-nitroperbenzoate
    Andrus, MB
    Zhou, ZN
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (30) : 8806 - 8807
  • [5] Palladium-Catalyzed Direct Ethynylation of C(sp3)-H Bonds in Aliphatic Carboxylic Acid Derivatives
    Ano, Yusuke
    Tobisu, Mamoru
    Chatani, Naoto
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) : 12984 - 12986
  • [6] Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds
    Baudoin, Olivier
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 4902 - 4911
  • [7] Bergman RG, 2007, NATURE, V446, P391, DOI 10.1038/446391a
  • [8] No stirring necessary: Parallel carbonylation of aryl halides with CO and various alcohols under pressure
    Blaser, HU
    Diggelmann, M
    Meier, H
    Naud, F
    Scheppach, E
    Schnyder, A
    Studer, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (09): : 3725 - 3728
  • [9] Cyclization by Catalytic Ruthenium Carbene Insertion into Csp3-H Bonds
    Cambeiro, Fermin
    Lopez, Susana
    Varela, Jesus A.
    Saa, Carlos
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (03) : 723 - 727
  • [10] Campeau LC, 2006, CHEM COMMUN, V1253