Palladium-catalyzed, aminoquinoline-directed arylation of phosphonamidate and phosphinic amide sp3 C-H bonds

被引:15
|
作者
Tung Thanh Nguyen [1 ]
Daugulis, Olafs [1 ]
机构
[1] Univ Houston, Dept Chem, Univ Pk, Houston, TX 77204 USA
关键词
CARBON-HYDROGEN BONDS; CYCLIZATION; ACTIVATION; FUNCTIONALIZATION; ALKYLATION; PHENOLS; OXIDES; SP(2); SCOPE;
D O I
10.1039/c7cc02063e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Aminoquinoline-directed, palladium-catalyzed sp(3) C-H bond arylation in phosphonamidates and phosphinic amides is reported. The reaction employs Pd(OAc)(2) as a catalyst at 10 mol% loading and cesium phosphate or potassium carbonate as a base in 1,2-dichlorobenzene as a solvent. The directing group can be removed under basic conditions to afford phosphonic acid esters. The chemistry described here is the first example of unactivated sp(3) C-H bond arylation by using a phosphorus-containing directing group.
引用
收藏
页码:4609 / 4611
页数:3
相关论文
共 50 条
  • [21] Palladium-Catalyzed Remote C(sp3)-H Arylation of 3-Pinanamine
    Cui, Wei
    Chen, Shengwei
    Wu, Jia-Qiang
    Zhao, Xin
    Hu, Wenhui
    Wang, Honggen
    ORGANIC LETTERS, 2014, 16 (16) : 4288 - 4291
  • [22] Palladium-catalyzed oxygenation of C(sp2)-H and C(sp3)-H bonds under the assistance of oxalyl amide
    Liu, Pei
    Han, Jian
    Chen, Chang Peng
    Shi, Da Qing
    Zhao, Ying Sheng
    RSC ADVANCES, 2015, 5 (36) : 28430 - 28434
  • [23] Challenge and progress: palladium-catalyzed sp3 C-H activation
    Li, Hu
    Lia, Bi-Jie
    Shi, Zhang-Jie
    CATALYSIS SCIENCE & TECHNOLOGY, 2011, 1 (02) : 191 - 206
  • [24] Palladium-Catalyzed Picolinamide-Directed Acetoxylation of Unactivated γ-C(sp3)-H Bonds of Alkylamines
    Li, Qiong
    Zhang, Shu-Yu
    He, Gang
    Nack, William A.
    Chen, Gong
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) : 1544 - 1548
  • [25] Palladium Catalyzed Arylation of C(sp3)-H Bonds of Carbonyl β-position in Water
    Luo Feihua
    Long Yang
    Li Zhengkai
    Zhou Xiangge
    ACTA CHIMICA SINICA, 2016, 74 (10) : 805 - 810
  • [26] Palladium-catalyzed methylation and arylation of sp2 and sp 3 C-H bonds in simple carboxylic acids
    Giri, Ramesh
    Maugel, Nathan
    Li, Jiao-Jie
    Wang, Dong-Hui
    Breazzano, Steven P.
    Saunders, Lindsey B.
    Yu, Jin-Quan
    Journal of the American Chemical Society, 2007, 129 (12): : 3510 - 3511
  • [27] Palladium-Catalyzed Decarboxylative Arylation of C-H Bonds by Aryl Acylperoxides
    Yu, Wing-Yiu
    Sit, Wing Nga
    Zhou, Zhongyuan
    Chan, Albert S. -C.
    ORGANIC LETTERS, 2009, 11 (15) : 3174 - 3177
  • [28] Palladium-Catalyzed Intramolecular Carbene Insertion into C(sp3)-H Bonds
    Sole, Daniel
    Mariani, Francesco
    Bennasar, M. -Lluisa
    Fernandez, Israel
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (22) : 6467 - 6470
  • [29] Palladium-Catalyzed Oxidative Carbonylation of Benzylic C-H Bonds via Nondirected C(sp3)-H Activation
    Xie, Pan
    Xie, Yinjun
    Qian, Bo
    Zhou, Han
    Xia, Chungu
    Huang, Hanmin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (24) : 9902 - 9905
  • [30] Amide-directed arylation of sp3 C-H bonds using Pd(II) and Pd(0) catalysts
    Wasa, Masayuki
    Yu, Jin-Quan
    TETRAHEDRON, 2010, 66 (26) : 4811 - 4815