Visible light mediated intermolecular [3+2] annulation of cyclopropylanilines with alkynes

被引：48
作者：
Nguyen, Theresa H. [1 ]
Maity, Soumitra [1 ]
Zheng, Nan [1 ]
机构：
[1] Univ Arkansas, Dept Chem & Biochem, Fayetteville, AR 72701 USA
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 10卷
基金：
美国国家卫生研究院; 美国国家科学基金会;
关键词：
3+2; alkyne; annulation; cyclopropylaniline; photoredox catalysis; visible light; PHOTOREDOX CATALYSIS; TERTIARY AMINOCYCLOPROPANES; N-CYCLOPROPYLANILINES; MECHANISTIC PROBES; AEROBIC OXIDATION; RING; DERIVATIVES; RADICALS; ROUTES;
D O I：
10.3762/bjoc.10.96
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Intermolecular [3 + 2] annulation of cyclopropylanilines with alkynes is realized using visible light photoredox catalysis, yielding a variety of cyclic allylic amines in fair to good yields. This method exhibits significant group tolerance particularly with heterocycles. It can also be used to prepare complex heterocycles such as fused indolines.
引用
收藏
页码：975 / 980
页数：6
相关论文
共 50 条
  • [21] Visible-Light-Driven [3+2]/[4+2] Annulation Reactions of Alkenes with N-Aminopyridinium Salts
    Wang, Yu-Zhao
    Liang, Peng-Yu
    Liu, Hong-Chao
    Lin, Wu-Jie
    Zhou, Pan-Pan
    Yu, Wei
    ORGANIC LETTERS, 2022, : 6037 - 6042
  • [22] Palladium-Catalyzed Double Decarboxylative [3+2] Annulation of Naphthalic Anhydrides with Internal Alkynes
    Kanganavaree, Chaipot
    Kantarod, Kritchasorn
    Worakul, Thanapat
    Soorukram, Darunee
    Kuhakarn, Chutima
    Chakarawet, Khetpakorn
    Wattanathana, Worawat
    Surawatanawong, Panida
    Reutrakul, Vichai
    Leowanawat, Pawaret
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (20) : 15083 - 15090
  • [23] Visible-light-induced synthesis of benzothiophenes and benzoselenophenes via the annulation of thiophenols or 1,2-diphenyldiselane with alkynes
    Xia, Xiao-Feng
    Zhang, Guo-Wei
    Zhu, Su-Li
    TETRAHEDRON, 2017, 73 (19) : 2727 - 2730
  • [24] Visible Light-Induced [3+2] Annulation Reaction of Alkenes with Vinyl Azides: Direct Synthesis of Functionalized Pyrroles
    Yang, Ming
    Wang, Xin-Yu
    Wang, Jie
    Zhao, Yu-Long
    CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (02) : 151 - 156
  • [25] Trifluoroethylation of Alkynes: Synthesis of Allylic-CF3 Compounds by Visible-Light Photocatalysis
    Roh, Geum-bee
    Iqbal, Naeem
    Cho, Eun Jin
    CHINESE JOURNAL OF CHEMISTRY, 2016, 34 (05) : 459 - 464
  • [26] Visible-light organophotoredox-mediated intermolecular formal [4+2] cycloadditions of arylcyclobutylamines with olefins
    Luo, Zhengshan
    Xing, Zequn
    Gao, Rui
    Han, Yufang
    Ren, Jun
    Wang, Zhongwen
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (22) : 4637 - 4642
  • [27] Ruthenium(II)-Catalyzed C-H Bond [3+2] Annulation of N-Nitrosoanilines with Alkynes in Water
    Chen, Xun
    Cui, Xue
    Bai, Lili
    Wang, Ying
    Xie, Ying
    Wang, Shuojin
    Zhai, Ruirui
    Zhao, Ke
    Kong, Dulin
    Li, Youbin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (12) : 2209 - 2212
  • [28] Visible light mediated azomethine ylide formation-photoredox catalyzed [3+2] cycloadditions
    Rueping, Magnus
    Leonori, Daniele
    Poisson, Thomas
    CHEMICAL COMMUNICATIONS, 2011, 47 (34) : 9615 - 9617
  • [29] A visible-light-induced intermolecular [3+2] alkenylation-cyclization strategy: metal-free construction of pyrrolo[2,1,5-cd]indolizine rings
    Liang, Yaofeng
    Teng, Lili
    Wang, Yajun
    He, Qiuxing
    Cao, Hua
    GREEN CHEMISTRY, 2019, 21 (15) : 4025 - 4029
  • [30] Visible-Light-Accelerated Copper-Catalyzed [3+2] Cycloaddition ofN-Tosylcyclopropylamines with Alkynes/Alkenes
    Kumar, Manoj
    Verma, Shalini
    Mishra, Vivek
    Reiser, Oliver
    Verma, Akhilesh K.
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (09) : 6263 - 6272
12345