Visible-Light-Photocatalyzed Metal-Free C-H Heteroarylation of Heteroarenes at Room Temperature: A Sustainable Synthesis of Biheteroaryls

被引:65
|
作者
Maity, Pintu [1 ]
Kundu, Debasish [1 ]
Ranu, Brindaban C. [1 ]
机构
[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, India
关键词
Synthetic methods; Photochemistry; C-H heteroarylation; Cross-coupling; Heterocycles; Radical reactions; CROSS-COUPLING REACTION; ARYL DIAZONIUM SALTS; PHOTOREDOX CATALYSIS; DIRECT ARYLATIONS; DIRECT CONVERSION; BORONIC ACIDS; EOSIN Y; AMINO; ANILINES; TRIFLUOROMETHYLATION;
D O I
10.1002/ejoc.201500006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient C-H heteroarylation of heteroarenes is achieved through visible-light photoredox-catalyzed diazotization of heteroarylamines in situ by tBuONO at room temperature. A library of functionalized biheteroaryls is obtained by using this protocol. The reaction avoids the use of transition-metal catalysts, additives, and acidic reaction medium.
引用
收藏
页码:1727 / 1734
页数:8
相关论文
共 50 条
  • [21] Metal-Free C-H Amination for Indole Synthesis
    Jang, Young Ho
    Youn, So Won
    ORGANIC LETTERS, 2014, 16 (14) : 3720 - 3723
  • [22] Boron Recycling in the Metal-Free Transfer C-H Borylation of Terminal Alkynes and Heteroarenes
    Desrosiers, Vincent
    Garcia, Cecilia Zavaleta
    Fontaine, Frederic-Georges
    ACS CATALYSIS, 2020, 10 (19): : 11046 - 11056
  • [23] Metal-Free Direct C-H Perfluoroalkylation of Arenes and Heteroarenes Using a Photoredox Organocatalyst
    Cui, Lei
    Matusaki, Yoko
    Tada, Norihiro
    Miura, Tsuyoshi
    Uno, Bunji
    Itoh, Akichika
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (11-12) : 2203 - 2207
  • [24] Transition metal-free C-H activation of heteroarenes: an overview (2018-2022)
    Habib, Imran
    Singha, Koustav
    Hossain, Mossaraf
    SYNTHETIC COMMUNICATIONS, 2023, 53 (01) : 1 - 22
  • [25] Visible Light Photocatalytic Metal-Free Perfluoroalkylation of Heteroarenes in Continuous Flow
    Straathof, Natan J. W.
    van Osch, Dannie J. G. P.
    Schouten, Arian
    Wang, Xiao
    Schouten, Jaap C.
    Hessel, Volker
    Noel, Timothy
    JOURNAL OF FLOW CHEMISTRY, 2014, 4 (01) : 12 - 17
  • [26] Visible Light Photocatalytic Metal-Free Perfluoroalkylation of Heteroarenes in Continuous Flow
    Natan J. W. Straathof
    Dannie J. G. P. van Osch
    Arian Schouten
    Xiao Wang
    Jaap C. Schouten
    Volker Hessel
    Timoth Noël
    Journal of Flow Chemistry, 2014, 4 : 12 - 17
  • [27] Metal-free visible light mediated direct C-H amination of benzoxazole with secondary amines
    Beg, Mohd. Zaheeruddin
    Singh, Pravin K.
    Singh, Praveen P.
    Srivastava, Manish
    Srivastava, Vishal
    MOLECULAR DIVERSITY, 2024, 28 (01) : 61 - 71
  • [28] Visible-Light-Promoted Metal-Free Photocatalytic Direct Aromatic C-H Oxygenation
    Bhuyan, Samuzal
    Gogoi, Abhijit
    Basumatary, Joneswar
    Roy, Biswajit Gopal
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (16)
  • [29] Metal-free, visible-light driven C-H ketoalkylation of glycine derivatives and peptides
    Xin, Hong
    Yuan, Zi-Hang
    Yang, Mingyu
    Wang, Ming-Hua
    Duan, Xin-Hua
    Guo, Li-Na
    GREEN CHEMISTRY, 2021, 23 (23) : 9549 - 9553
  • [30] Visible-Light-Photocatalyzed C5-H Nitration of 8-Aminoquinoline Amides
    Liu, Pugen
    Qiao, Huijie
    Su, Xiaoxue
    Bai, Peirong
    Yang, Fan
    CATALYSTS, 2024, 14 (04)