Access to cyano-substituted pyrazolines through copper-catalyzed cascade cyanation/cyclization of unactivated olefins

被引：15
|
作者：
Meng, Fei [1 ,2 ]
Fang, Qin [1 ,2 ]
Yuan, Weidong [1 ,2 ]
Xu, Ning [1 ,2 ]
Cao, Shujun [1 ,2 ]
Chun, Jianlin [1 ,2 ]
Li, Jie [1 ,2 ]
Zhang, Honglin [1 ,2 ]
Zhu, Yingguang [1 ,2 ]
机构：
[1] Nanjing Agr Univ, Jiangsu Key Lab Pesticide Sci, Coll Sci, Nanjing 210095, Peoples R China
[2] Nanjing Agr Univ, Dept Chem, Coll Sci, Nanjing 210095, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2020年 / 7卷 / 11期
基金：
中国国家自然科学基金;
关键词：
C-H CYANATION; N-RADICAL CASCADE; INTRAMOLECULAR AMINOCYANATION; OXIDATIVE CYANATION; ALKENES SYNTHESIS; BOND FORMATION; ARENES; DIFUNCTIONALIZATION; DIAMINATION; PALLADIUM;
D O I：
10.1039/d0qo00282h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel and efficient copper-catalyzed domino cyanation/cyclization of hydrazone-tethered unactivated olefins has been developed. A range of cyano-containing pyrazolines have been easily obtained in good yields under mild conditions. This method provides a facile, practical, and rapid access to valuable pyrazolines with the important cyano functionality, and it is amenable for gram scale synthesis. The simultaneous formation of C(sp(3))-CN and C-N bonds can be achieved in a single step.
引用
收藏
页码：1358 / 1364
页数：7
相关论文
共 50 条
  • [31] Copper-Catalyzed Amide Radical-Directed Cyanation of Unactivated Csp3-H Bonds
    Zhang, Hongwei
    Zhou, Yulu
    Tian, Peiyuan
    Jiang, Cuiyu
    ORGANIC LETTERS, 2019, 21 (06) : 1921 - 1925
  • [32] Copper-Catalyzed Aminoheteroarylation of Unactivated Alkenes through Distal Heteroaryl Migration
    Kwon, Yungeun
    Zhang, Wei
    Wang, Qiu
    ACS CATALYSIS, 2021, 11 (14): : 8807 - 8817
  • [33] Copper-Catalyzed Cascade Addition/Cyclization: An Efficient and Versatile Synthesis of N-Substituted 2-Heterobenzimidazoles
    Lv, Xin
    Bao, Weiliang
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15): : 5618 - 5621
  • [34] Nucleophilic Substitution at Unactivated Arene C-H: Copper-Catalyzed anti-Selective Silylative Cyclization of Substituted Benzylacetylenes
    Moniwa, Hirokazu
    Shintani, Ryo
    ORGANIC LETTERS, 2025, 27 (07) : 1763 - 1768
  • [35] Copper-catalyzed cascade click/nucleophilic substitution reaction to access fully substituted triazolyl-organosulfurs
    Li, Ming
    Dong, Kun
    Zheng, Yubin
    Song, Wangze
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (46) : 9933 - 9941
  • [36] Copper-Catalyzed Oxidative Trifunctionalization of Olefins: An Access to Functionalized β-Keto Thiosulfones
    Huang, Shuai
    Thirupathi, Nuligonda
    Tung, Chen-Ho
    Xu, Zhenghu
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (16): : 9449 - 9455
  • [37] Copper-catalyzed Tandem Cyclization to Access 4-Aminoquinoline Derivatives
    Sheng, Hui-Yang
    Chen, Hui
    Liao, Meng
    Peng, Na
    Yang, Mian
    Cai, Qun
    Liu, Yi
    CHEMISTRY LETTERS, 2020, 49 (05) : 526 - 529
  • [38] Directed Copper-Catalyzed Intermolecular Heck-Type Reaction of Unactivated Olefins and Alkyl Halides
    Tang, Chunlin
    Zhang, Ran
    Zhu, Bo
    Fu, Junkai
    Deng, Yi
    Tian, Li
    Guan, Wei
    Bi, Xihe
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (49) : 16929 - 16935
  • [39] Copper-Catalyzed Cascade Cyclization of 2-Nitrochalcones with NH-Heterocycles
    Ly, Thang M.
    Huynh, Tan N.
    Phan, Nhi H. Y.
    Dinh, Phuong T.
    Nguyen, Tung T.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (23): : 17346 - 17354
  • [40] Recyclable copper-catalyzed cyclization of o-haloanilides and metal sulfides: An efficient and practical access to substituted benzothiazoles
    Cai, Mingzhong
    Ye, Qian
    Huang, Wencheng
    Hao, Wenyan
    MOLECULAR CATALYSIS, 2022, 519
12345