Metal-free C-3 selective C(sp2)-C(sp3) heteroarylation of anilines with imidazo[1,2-a]pyridine derivatives via cross-dehydrogenative coupling

被引:2
|
作者
Wang, Kai [1 ,2 ]
Du, Xiaoxue [1 ,2 ]
Zhang, Pengfei [3 ]
Wei, Zhenjiang [4 ]
Cao, Xian-Ting [1 ,2 ]
机构
[1] Jining Med Univ, Coll Med Engn, Jining 272067, Peoples R China
[2] Jining Med Univ, Key Lab Med Funct Nanomat, Jining 272067, Peoples R China
[3] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Key Lab Organosilicon Chem & Mat Technol, Hangzhou 311121, Peoples R China
[4] Shandong Med Technician Coll, Dept Pharmaceut Engn, Tai An 271016, Peoples R China
关键词
C-H; BOND FORMATION; N-HYDROXYPHTHALIMIDE; WATER; HETEROCYCLES; ACTIVATION; ALKYLATION; AMINATION; EVOLUTION; STRATEGY;
D O I
10.1039/d3ra03852a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A general and straightforward method for the regioselective construction of C-3 heteroaryl-containing imidazo[1,2-a]pyridines via cross-dehydrogenative coupling under transition-metal-free conditions has been reported, utilizing N,N-dimethylaniline as the methylenation source and furnishing the C(sp(2))-C(sp(3)) functionalized products in good to excellent yields. Mechanism studies indicate that a radical pathway is responsible for this transformation.
引用
收藏
页码:21685 / 21689
页数:5
相关论文
共 50 条
  • [31] Bu4NI-catalyzed, oxidative C(sp2)-C(sp3)cross dehydrogenative coupling for the regioselective direct C-3 benzylation of 2H-indazoles
    Yadav, Lalit
    Chaudhary, Sandeep
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (30) : 5927 - 5936
  • [32] Photoinduced Nickel-Catalyzed Deaminative Cross-Electrophile Coupling for C(sp2)-C(sp3) and C(sp3)-C(sp3) Bond Formation
    Yang, Tao
    Wei, Yi
    Koh, Ming Joo
    ACS CATALYSIS, 2021, 11 (11): : 6519 - 6525
  • [33] Metal-free Cross-Dehydrogenative Coupling of HN-azoles with α-C(sp3)-H Amides via C-H Activation and Its Mechanistic and Application Studies
    Aruri, Hariprasad
    Singh, Umed
    Kumar, Mukesh
    Sharma, Sumit
    Aithagani, Sravan Kumar
    Gupta, Vivek K.
    Mignani, Serge
    Vishwakarma, Ram A.
    Singh, Parvinder Pal
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (02): : 1000 - 1012
  • [34] Transition-Metal-Free Radical C(sp3)-C(sp2) and C(sp3)-C(sp3) Coupling Enabled by 2-Azaallyls as Super-Electron-Donors and Coupling-Partners
    Li, Minyan
    Berritt, Simon
    Matuszewski, Lucas
    Deng, Guogang
    Pascual-Escudero, Ana
    Panetti, Grace B.
    Poznik, Michal
    Yang, Xiaodong
    Chruma, Jason J.
    Walsh, Patrick J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (45) : 16327 - 16333
  • [35] Copper porphyrin catalyzed esterification of C(sp3)-H via a cross-dehydrogenative coupling reaction
    Wang, Hua-Hua
    Wen, Wei-Hong
    Zou, Huai-Bo
    Cheng, Fan
    Ali, Atif
    Shi, Lei
    Liu, Hai-Yang
    Chang, Chi-Kwong
    NEW JOURNAL OF CHEMISTRY, 2017, 41 (09) : 3508 - 3514
  • [36] Nitrimines as Reagents for Metal-Free Formal C(sp2)-C(sp2) Cross-Coupling Reactions
    Angeles-Dunham, Veronica V.
    Nickerson, David M.
    Ray, Devin M.
    Mattson, Anita E.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (52) : 14538 - 14541
  • [37] Metal-Free Cyclopropanol Ring-Opening C(sp3)-C(sp2) Cross-Couplings with Aryl Sulfoxides
    Chen, Dengfeng
    Fu, Yuanyuan
    Cao, Xiaoji
    Luo, Jinyue
    Wang, Fei
    Huang, Shenlin
    ORGANIC LETTERS, 2019, 21 (14) : 5600 - 5605
  • [38] Acceptorless cross-dehydrogenative coupling for C(sp3)-H heteroarylation mediated by a heterogeneous GaN/ketone photocatalyst/photosensitizer system
    Hyotaik Kang
    Lida Tan
    Jing-Tan Han
    Chia-Yu Huang
    Hui Su
    Aleksei Kavun
    Chao-Jun Li
    Communications Chemistry, 6
  • [39] Acceptorless cross-dehydrogenative coupling for C(sp3)-H heteroarylation mediated by a heterogeneous GaN/ketone photocatalyst/photosensitizer system
    Kang, Hyotaik
    Tan, Lida
    Han, Jing-Tan
    Huang, Chia-Yu
    Su, Hui
    Kavun, Aleksei
    Li, Chao-Jun
    COMMUNICATIONS CHEMISTRY, 2023, 6 (01)
  • [40] Direct para-C-H heteroarylation of anilines with quinoxalinones by metal-free cross-dehydrogenative coupling under an aerobic atmosphere
    Xu, Jun
    Huang, Lin
    He, Lei
    Liang, Chenfeng
    Ouyang, Yani
    Shen, Jiabin
    Jiang, Min
    Li, Wanmei
    GREEN CHEMISTRY, 2021, 23 (17) : 6632 - 6638