A visible-light-promoted cross-dehydrogenative-coupling reaction of N-arylglycine esters with imidazo[1,2-a]pyridines

被引：26
|
作者：
Zhu, Zhi-Qiang [1 ,2 ]
Xiao, Li-Jin [2 ]
Zhou, Chun-Cheng [2 ]
Song, Han-Lin [2 ]
Xie, Zong-Bo [2 ]
Le, Zhang-Gao [1 ,2 ]
机构：
[1] East China Univ Technol, State Key Lab Breeding Base Nucl Resources & Envi, Nanchang 330013, Jiangxi, Peoples R China
[2] East China Univ Technol, Sch Chem Biol & Mat Sci, Nanchang 330013, Jiangxi, Peoples R China
来源：
TETRAHEDRON LETTERS | 2018年 / 59卷 / 35期
基金：
中国博士后科学基金; 中国国家自然科学基金;
关键词：
Copper; Visible light; Cross-dehydrogenative-coupling; Glycine ester; Imidazo[1,2-a]pyridine; TRANSFER RADICAL-ADDITION; AMINO CARBONYL-COMPOUNDS; PHOTOREDOX CATALYSIS; GLYCINE DERIVATIVES; TRANSITION-METAL; ACID CATALYSIS; COPPER; IMIDAZOHETEROCYCLES; FUNCTIONALIZATION; ATOM;
D O I：
10.1016/j.tetlet.2018.07.047
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A mild and convenient visible-light-promoted cross-dehydrogenative-coupling reaction between N-arylglycine esters and imidazo[1,2-a]pyridines for the construction of C-C bond was developed. A range of N-arylglycine esters and imidazo[1,2-a]pyridines were able to undergo the CDC reaction readily to afford alpha-heteroaryl substituted alpha-amino acid derivatives in good to excellent yields. A tentative mechanism for the photoredox reaction was also proposed. Importantly, the use of copper(II) salt as the sole catalyst in this visible-light-promoted transformation makes this reaction sustainable and practical. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3326 / 3331
页数：6
相关论文
共 50 条
  • [1] A Highly Efficient Copper(II)-Catalyzed Cross-Dehydrogenative-Coupling Reaction of N-Arylglycine Esters with 2-Arylimidazo[1,2-a]pyridines
    Zhu, Zhi-Qiang
    Xiao, Li-Jin
    Chen, Ying
    Xie, Zong-Bo
    Zhu, Hai-Bo
    Le, Zhang-Gao
    [J]. SYNTHESIS-STUTTGART, 2018, 50 (14): : 2775 - 2783
  • [2] Copper-Catalyzed Cross-Dehydrogenative-Coupling Reaction of N-Arylglycine Esters with Imides or Amides for Synthesis of α-Substituted α-Amino Acid Esters
    Xiao, Li-Jin
    Zhu, Zhi-Qiang
    Guo, Dong
    Xie, Zong-Bo
    Lu, Yue
    Le, Zhang-Gao
    [J]. SYNLETT, 2018, 29 (12) : 1659 - 1663
  • [3] Photosensitizer-Free Visible-Light-Promoted Trifluoromethylation of Imidazo[1,2-a]pyridines
    Yao, Ruichaoa
    Chen, Wenbo
    Shen, Qilong
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (07) : 2684 - 2692
  • [4] Palladium-Catalyzed α-Selective Alkenylation of Imidazo[1,2-a]pyridines through Aerobic Cross-Dehydrogenative Coupling Reaction
    Ghosh, Monoranjan
    Naskar, Aswini
    Mitra, Shubhanjan
    Hajra, Alakananda
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (04) : 715 - 718
  • [5] Visible-Light-Promoted Direct Amination of Phenols via Oxidative Cross-Dehydrogenative Coupling Reaction
    Zhao, Yating
    Huang, Binbin
    Yang, Chao
    Xia, Wujiong
    [J]. ORGANIC LETTERS, 2016, 18 (14) : 3326 - 3329
  • [6] TEMPO-Mediated Cross-Dehydrogenative Coupling of Indoles and Imidazo[1,2-a]pyridines with Fluorinated Alcohols
    Nipate, Dhananjay S.
    Jaspal, Sonam
    Shinde, Vikki N.
    Rangan, Krishnan
    Kumar, Anil
    [J]. ORGANIC LETTERS, 2021, 23 (04) : 1373 - 1377
  • [7] Synthesis of β-hydroxy-α-amino acid derivatives by the cross-dehydrogenative coupling of N-arylglycine esters with α-hydroxy ketones
    Wang, Junjiao
    Lv, Yuyu
    Shang, Yongwei
    Deng, Zhoubin
    Zhang, Jianzhong
    Ma, Xue-E
    Wang, Ke-Hu
    Huang, Danfeng
    Su, Yingpeng
    Hu, Yulai
    [J]. TETRAHEDRON, 2021, 100
  • [8] Visible-Light-Induced Dehydrogenative Imidoylation of Imidazo[1,2-a]pyridines with α-Amino Acid Derivatives and α-Amino Ketones
    Zhu, Zhi-Qiang
    Guo, Dong
    Ji, Jiu-Jian
    Zhu, Xiao
    Tang, Juan
    Xie, Zong-Bo
    Le, Zhang-Gao
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (23): : 15062 - 15071
  • [9] Visible-light-promoted sodium iodide-mediated sulfenylation of imidazo [1,2-a]pyridines heterocycle using thiosulfate as odorless electrophilic arylsulphenyl source
    Xie, Zhen
    Li, Mengxin
    Zhao, Molai
    Wen, Xiaoqing
    Lin, Li
    Jiang, Hezhong
    Hou, Zongrui
    Li, Jiahong
    [J]. TETRAHEDRON LETTERS, 2024, 136
  • [10] Vertically-expanded imidazo[1,2-a]pyridines and imidazo[1,5-a]pyridine via dehydrogenative coupling
    Firmansyah, Dikhi
    Banasiewicz, Marzena
    Gryko, Daniel T.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (05) : 1367 - 1374
12345