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
来源：
CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 33期
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
  • [11] Palladium-Catalyzed C(sp3)-H Arylation and Alkynylation of Peptides Directed by Aspartic Acid (Asp)
    Chen, Zhuo
    Zhu, Meijie
    Cai, Mengwei
    Xu, Lulu
    Weng, Yiyi
    ACS CATALYSIS, 2021, 11 (12) : 7401 - 7410
  • [12] Aminoquinoline-directed, cobalt-catalyzed carbonylation of sulfonamide sp2 C-H bonds
    Tung Thanh Nguyen
    Grigorjeva, Liene
    Daugulis, Olafs
    CHEMICAL COMMUNICATIONS, 2017, 53 (37) : 5136 - 5138
  • [13] Palladium-catalyzed methylene C(sp3)-H arylation of the adamantyl scaffold
    Lao, Ye-Xing
    Wu, Jia-Qiang
    Chen, Yunyun
    Zhang, Shang-Shi
    Li, Qingjiang
    Wang, Honggen
    ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (10): : 1374 - 1378
  • [14] Palladium-Catalyzed β-Arylation of Amide via Primary sp3C-H Activation
    Zhao, Ren
    Lu, Wenjun
    ORGANOMETALLICS, 2018, 37 (13) : 2188 - 2192
  • [15] 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
  • [16] 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
  • [17] 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
  • [18] 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
  • [19] Palladium-Catalyzed γ-C(sp3)-H Arylation of Thiols by a Detachable Protecting/Directing Group
    Jin, Likun
    Wang, Jianchun
    Dong, Guangbin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (38) : 12352 - 12355
  • [20] 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
12345