Palladium-Catalyzed C-H Olefination of Imidazo[1,2a] pyridine Carboxamide in Aqueous Ethanol under Oxygen

被引:1
|
作者
Mohite, Sachin Balaso [1 ]
Mirza, Yafia Kousin [3 ]
Kumar, Vishal [1 ]
Partap, Sangh [1 ]
Baji Baba, Shaik [1 ]
Alake, John [1 ]
Bera, Milan [2 ,3 ]
Karpoormath, Rajshekhar [1 ]
机构
[1] Univ KwaZulu Natal Westville, Coll Hlth Sci, Dept Pharmaceut Chem, Discipline Pharmaceut Sci, ZA-4000 Durban, South Africa
[2] Amity Univ, Photocatalysis & Synthet Methodol Lab PSML, Noida 201303, India
[3] Amity Univ, Amity Inst Click Chem Res & Studies AICCRS, Noida 201303, India
基金
新加坡国家研究基金会;
关键词
Sustainable C-H alkenylation; Palladium; H2O tolerant; regioselective; Imidazo[1,2a] pyridine; ACTIVATION; FUNCTIONALIZATION; DIOLEFINATION; ARENES; WATER; AIR;
D O I
10.1002/chem.202304239
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The advancement of sustainable chemistry and changes in the economy are strongly intertwined. Reaction time, cost savings, moderate temperatures, and generation of the fewest byproducts are frequently achieved by using catalytic processes. Herein, we report the C-H olefination of imidazo[1,2a] pyridine carboxamides with various acrylates in the presence of Pd (OAc)(2 )with O(2 )as the oxidant in aqueous ethanol rather than using non-ecofriendly solvents. The C-H activation features most user-friendly reaction conditions, excellent yield as well as plenty substrate scope and applicable for C-H deuteriation of the corresponding heteroarenes with D2O. Experimental mechanistic studies indicate that C-H activation step succeeded after formation of tetra coordinated square planer Pd-substrate adduct.
引用
收藏
页数:6
相关论文
共 50 条
  • [31] Palladium-Catalyzed C-H Functionalization Using Guanidine as a Directing Group: Ortho Arylation and Olefination of Arylguanidines
    Shao, Jiaan
    Chen, Wenteng
    Giulianotti, Marc A.
    Houghten, Richard A.
    Yu, Yongping
    ORGANIC LETTERS, 2012, 14 (21) : 5452 - 5455
  • [32] Experimental and Computational Studies on the Directing Ability of Chalcogenoethers in Palladium-Catalyzed Atroposelective C-H Olefination and Allylation
    Liao, Gang
    Zhang, Tao
    Jin, Liang
    Wang, Bing-Jie
    Xu, Cheng-Kai
    Lan, Yu
    Zhao, Yu
    Shi, Bing-Feng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (10)
  • [33] Dienyl esters synthesis: Palladium-catalyzed C-H olefination of electron-deficient alkenes with allenoates
    Xia, Xiao-Feng
    Zhu, Su-Li
    Hu, Qingtao
    Li, Yanzhao
    Xu, Xiang
    TETRAHEDRON, 2017, 73 (25) : 3529 - 3535
  • [34] Palladium-Catalyzed C-H Homocoupling of Furans and Thiophenes Using Oxygen as the Oxidant
    Li, Na-Na
    Zhang, Yan-Lei
    Mao, Shuai
    Gao, Ya-Ru
    Guo, Dong-Dong
    Wang, Yong-Qiang
    ORGANIC LETTERS, 2014, 16 (10) : 2732 - 2735
  • [35] Palladium-catalyzed remote meta-C-H olefination of cinnamates
    Bakthadoss, Manickam
    Hussain, Mir Ashiq
    Reddy, Tadiparthi Thirupathi
    CHEMICAL COMMUNICATIONS, 2023, 59 (35) : 5249 - 5252
  • [36] Palladium-catalyzed enantioselective C-H functionalization via C-H palladation
    Zhan, Bei-Bei
    Jin, Liang
    Shi, Bing-Feng
    TRENDS IN CHEMISTRY, 2022, 4 (03): : 220 - 235
  • [37] Palladium catalyzed selective distal C-H olefination of biaryl systems
    Maity, Soham
    Hoque, Ehtasimul
    Dhawa, Uttam
    Maiti, Debabrata
    CHEMICAL COMMUNICATIONS, 2016, 52 (97) : 14003 - 14006
  • [38] Cu-Catalyzed selective C3-formylation of imidazo[1,2-a]pyridine C-H bonds with DMSO using molecular oxygen
    Cao, Hua
    Lei, Sai
    Li, Naiying
    Chen, Longbin
    Liu, Jingyun
    Cai, Huiyin
    Qiu, Shuxian
    Tan, Jingwen
    CHEMICAL COMMUNICATIONS, 2015, 51 (10) : 1823 - 1825
  • [39] Palladium-Catalyzed Regioselective Dehydrogenative C-H/C-H Cross-Coupling of Pyrroles and Pyridine N-Oxides
    Liu, Shanshan
    Tzschucke, C. Christoph
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (21) : 3509 - 3513
  • [40] Palladium-Catalyzed Electrooxidative Double C-H Arylation
    Lin, Zhipeng
    Oliveira, Joao C. A.
    Scheremetjew, Alexej
    Ackermann, Lutz
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 146 (01) : 228 - 239