Pd(II)-Catalyzed arylation of unactivated methylene C(sp3)-H bonds with aryl halides using a removable auxiliary

被引:80
作者
Zhang, Qi [1 ]
Yin, Xue-Song [1 ]
Zhao, Sheng [1 ]
Fang, Sheng-Long [1 ]
Shi, Bing-Feng [1 ,2 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
基金
美国国家科学基金会;
关键词
C-H BONDS; CATALYZED DIRECT ARYLATION; CARBON-HYDROGEN BONDS; COUPLING REACTIONS; DIRECTING GROUP; BETA-LACTAMS; PALLADIUM; FUNCTIONALIZATION; ACTIVATION; ALKYLATION;
D O I
10.1039/c4cc03615h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Pd(II)-catalyzed arylation of methylene C(sp(3))-H bonds in aliphatic amides directed by our newly developed PIP directing group with aryl iodides/bromides has been achieved. Arylation occurs efficiently with a broad range of aryl halides and amides.
引用
收藏
页码:8353 / 8355
页数:3
相关论文
共 50 条
  • [21] Amide-directed arylation of sp3 C-H bonds using Pd(II) and Pd(0) catalysts
    Wasa, Masayuki
    Yu, Jin-Quan
    [J]. TETRAHEDRON, 2010, 66 (26) : 4811 - 4815
  • [22] Palladium(II)-catalyzed arylation of unactivated C(sp3)-H bonds by using 2,1,3-benzoselenadiazole-4-amine as directing ligand
    Yan, Xufei
    Long, Rongrong
    Luo, Feihua
    Yang, Li
    Zhou, Xiangge
    [J]. TETRAHEDRON LETTERS, 2017, 58 (01) : 54 - 58
  • [23] Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds
    Baudoin, Olivier
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 4902 - 4911
  • [24] Pd(II)-catalyzed alkylation of unactivated C(sp3)-H bonds: efficient synthesis of optically active unnatural α-amino acids
    Chen, Kai
    Hu, Fang
    Zhang, Shuo-Qing
    Shi, Bing-Feng
    [J]. CHEMICAL SCIENCE, 2013, 4 (10) : 3906 - 3911
  • [25] Ligand-Enabled Pd(II)-Catalyzed ?-Methylene C(sp3)-H Arylation of Free Aliphatic Acids
    Hu, Liang
    Meng, Guangrong
    Yu, Jin-Quan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (45) : 20550 - 20553
  • [26] Pd-Catalyzed γ-C(sp3)-H Arylation of Free Amines Using a Transient Directing Group
    Wu, Yongwei
    Chen, Yan-Qiao
    Liu, Tao
    Eastgate, Martin D.
    Yu, Jin-Quan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (44) : 14554 - 14557
  • [27] Nickel-Catalyzed Ortho-Arylation of Unactivated (Hetero)aryl C-H Bonds with Arylsilanes Using a Removable Auxiliary
    Zhao, Sheng
    Liu, Bin
    Zhan, Bei-Bei
    Zhang, Wei-Dong
    Shi, Bing-Feng
    [J]. ORGANIC LETTERS, 2016, 18 (18) : 4586 - 4589
  • [28] Stereoselective Synthesis of β-Alkylated α-Amino Acids via Palladium-Catalyzed Alkylation of Unactivated Methylene C(sp3)-H Bonds with Primary Alkyl Halides
    Zhang, Shu-Yu
    Li, Qiong
    He, Gang
    Nack, William A.
    Chen, Gong
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (32) : 12135 - 12141
  • [29] Palladium Catalyzed Arylation of C(sp3)-H Bonds of Carbonyl β-position in Water
    Luo Feihua
    Long Yang
    Li Zhengkai
    Zhou Xiangge
    [J]. ACTA CHIMICA SINICA, 2016, 74 (10) : 805 - 810
  • [30] Palladium-Catalyzed Cs2CO3-Promoted Arylation of Unactivated C(sp3)-H Bonds by (Diacetoxyiodo)arenes: Shifting the Reactivity of (Diacetoxyiodo)arenes from Acetoxylation to Arylation
    Gou, Quan
    Zhang, Zhao-Fu
    Liu, Zhi-Cheng
    Qin, Jun
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (06) : 3176 - 3186