Pd-Catalyzed Oxidative ortho-C-H Borylation of Arenes

被引:160
|
作者
Dai, Hui-Xiong [1 ]
Yu, Jin-Quan [1 ]
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
关键词
DIRECTED ORTHO BORYLATION; CROSS-COUPLING REACTIONS; ARYL HALIDES; ROOM-TEMPERATURE; FUNCTIONALIZED ARENES; AROMATIC BORYLATION; DIBORON REAGENTS; BOND FORMATION; PALLADIUM; PINACOLBORANE;
D O I
10.1021/ja2097095
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The development of a Pd-catalyzed oxidative ortho-C-H borylation with N-arylbenzamides is reported. A modified dibenzylideneacetone (dba) ligand, a weak base, and a strong oxidant are critical for obtaining good yields. The reaction is tolerant of electron-deficient and electron-rich benzamides derived from readily available benzoic acids. The borylated products can be converted to various synthons via diverse transformations.
引用
收藏
页码:134 / 137
页数:4
相关论文
共 50 条
  • [1] Pd-Catalyzed Directed ortho-C-H Alkenylation of Phenylalanine Derivatives
    Garcia-Rubia, Alfonso
    Laga, Eduardo
    Cativiela, Carlos
    Urriolabeitia, Esteban P.
    Gomez-Arrayas, Ramon
    Carretero, Juan C.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (06): : 3321 - 3331
  • [2] Pd-Catalyzed ortho-C-H Olefination of Benzenesulfonamides Directed by 7-Azaindole
    Huo, Xing
    Han, Jun
    Yan, Xiaoxiao
    Zhang, Heng
    Xiong, Juan
    Liu, Jian
    Wang, Xiaolei
    Li, Huilin
    Huo, Leiming
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (12) : 2087 - 2091
  • [3] Pd-Catalyzed Intermolecular ortho-C-H Amidation of Anilides by N-Nosyloxycarbamate
    Ng, Ka-Ho
    Chan, Albert S. C.
    Yu, Wing-Yiu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (37) : 12862 - 12864
  • [4] Pd-Catalyzed regioselective sequential meta-, ortho-C-H functionalization of arenes: a predictable approach to the synthesis of polysubstituted β-arylethylamines
    Han, Jian
    Wang, Ning
    Huang, Zhi-Bin
    Zhao, Yingsheng
    Shi, Da-Qing
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (24) : 5112 - 5116
  • [5] Pd-Catalyzed π-Chelation Assisted ortho-C-H Activation and Annulation of Allylarenes with Internal Alkynes
    Gandeepan, Parthasarathy
    Cheng, Chien-Hong
    [J]. ORGANIC LETTERS, 2013, 15 (09) : 2084 - 2087
  • [6] Pd-Catalyzed Direct ortho-C-H Arylation of Aromatic Ketones Enabled by a Transient Directing Group
    Xu, Jiancong
    Liu, Yang
    Wang, Ying
    Li, Yajuan
    Xu, Xiaohua
    Jin, Zhong
    [J]. ORGANIC LETTERS, 2017, 19 (07) : 1562 - 1565
  • [7] Experiment and Computational Study on Pd-Catalyzed MIA-Directed Ortho-C-H Alkynlation of Phenylalanine
    Zhang, Fujie
    Liang, Yu
    Liu, Dong-Hui
    Liu, Peng-Yu
    Huang, Liangliang
    He, Yu-Peng
    Yu, Fang
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (07)
  • [8] Monodentate Transient Directing Group Enabled Pd-Catalyzed Ortho-C-H Methoxylation and Chlorination of Benzaldehydes
    Li, Feng
    Zhou, Yirong
    Yang, Heng
    Wang, Ziqi
    Yu, Qinqin
    Zhang, Fang-Lin
    [J]. ORGANIC LETTERS, 2019, 21 (10) : 3692 - 3695
  • [9] Ruthenium-Catalyzed ortho-C-H Hydroxyfluoroalkylation of Arenes with Fluorinated Alcohols
    Liu, Bo
    Chen, Xiaoyu
    Pei, Congcong
    Li, Jingya
    Zou, Dapeng
    Wu, Yangjie
    Wu, Yusheng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (21): : 14364 - 14373
  • [10] Rhodium-Catalyzed PIII-Directed ortho-C-H Borylation of Arylphosphines
    Wen, Jian
    Wang, Dingyi
    Qian, Jiasheng
    Wang, Di
    Zhu, Chendan
    Zhao, Yue
    Shi, Zhuangzhi
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (07) : 2078 - 2082