Regioselective 2-alkylation of indoles with α-bromo esters catalyzed by Pd/P,P=O system

被引:1
|
作者
Wei Tiana [1 ]
Bowen Li [1 ,2 ]
Duanshuai Tian [1 ]
Wenjun Tang [1 ,2 ]
机构
[1] State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry,University of Chinese Academy of Sciences
[2] School of Chemistry and Material Sciences, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences
基金
中国国家自然科学基金;
关键词
D O I
暂无
中图分类号
学科分类号
摘要
A palladium-catalyzed 2-alkylation of indoles with α-bromo esters is developed by employing a P,P=O ligand. The method features excellent regioselectivities, mild reaction conditions, and good functional group compatibility. The employment of the P,P=O ligand as well as 4 A molecular sieves were crucial for the success of the transformation. Mechanistic studies indicate the reaction proceed through a radical pathway.
引用
收藏
页码:197 / 200
页数:4
相关论文
共 50 条
  • [1] Regioselective 2-alkylation of indoles with α-bromo esters catalyzed by Pd/P,P=O system
    Tian, Wei
    Li, Bowen
    Tian, Duanshuai
    Tang, Wenjun
    [J]. CHINESE CHEMICAL LETTERS, 2022, 33 (01) : 197 - 200
  • [2] Pd(II)-Catalyzed Regioselective 2-Alkylation of Indoles via a Norbornene-Mediated C-H Activation: Mechanism and Applications
    Jiao, Lei
    Herdtweck, Eberhardt
    Bach, Thorsten
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (35) : 14563 - 14572
  • [3] Palladium-Catalyzed Direct 2-Alkylation of Indoles by Norbornene-Mediated Regioselective Cascade C-H Activation
    Jiao, Lei
    Bach, Thorsten
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) : 12990 - 12993
  • [4] Enantioselective Pd-catalyzed allylic alkylation of Indoles by a new class of chiral ferrocenyl P/S Ligands
    Cheung, Hong Yee
    Yu, Wing-Yiu
    Lam, Fuk Loi
    Au-Yeung, Terry T. -L.
    Zhou, Zhongyuan
    Chan, Tak Hang
    Chan, Albert S. C.
    [J]. ORGANIC LETTERS, 2007, 9 (21) : 4295 - 4298
  • [5] Pd(OAc)2-Catalyzed Regioselective Arylation of Indoles with Arylsiloxane in Acidic Medium
    Liang, Zunjun
    Yao, Bangben
    Zhang, Yuhong
    [J]. ORGANIC LETTERS, 2010, 12 (14) : 3185 - 3187
  • [6] Iodine-catalyzed regioselective C-3 arylation of indoles with p-quinols
    Neha Dua
    Rama Krishna Peddinti
    [J]. Journal of Chemical Sciences, 2020, 132
  • [7] Iodine-catalyzed regioselective C-3 arylation of indoles with p-quinols
    Dua, Neha
    Peddinti, Rama Krishna
    [J]. JOURNAL OF CHEMICAL SCIENCES, 2020, 132 (01)
  • [8] Memory and dynamics in Pd-catalyzed allylic alkylation with P,N-ligands
    Johansson, Charlotte
    Lloyd-Jones, Guy C.
    Norrby, Per-Ola
    [J]. TETRAHEDRON-ASYMMETRY, 2010, 21 (11-12) : 1585 - 1592
  • [9] α-arylation of esters catalyzed by the Pd(I) dimer {[P(t-Bu)3]PdBr}2
    Hama, Takuo
    Hartwig, John F.
    [J]. ORGANIC LETTERS, 2008, 10 (08) : 1545 - 1548
  • [10] Regioselective O-alkylation of 2-pyridones by TfOH-catalyzed carbenoid insertion
    Yan, Zhewei
    He, Hangli
    Yuan, Dabiao
    Yan, Qiongjiao
    Wang, Wei
    Jiang, Haipeng
    Wang, Haifeng
    Chen, Fener
    [J]. CHEMICAL COMMUNICATIONS, 2022, 59 (01) : 106 - 109