Visible-Light-Induced Tandem Cyclization of 1,7-Enynes to Access Phenanthridin-6(5H)-Ones Using a Polydimethylsiloxane (PDMS) Based Microreactor

被引：0
|
作者：
Ravi, Dharavath [1 ,2 ]
Prasad, Vadla Shiva [1 ,2 ]
Rao, Vadithya Ranga [1 ,2 ]
Krishna, Silari Mohana [1 ,2 ]
Kumar, Chelukalapally Anil [1 ]
Saha, Biswajit [3 ]
Adiyala, Praveen Reddy [1 ,2 ]
机构：
[1] CSIR Indian Inst Chem Technol CSIR IICT, Dept Organ Synth & Proc Chem, Hyderabad 500007, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
[3] CSIR Indian Inst Chem Technol CSIR IICT, Dept Appl Biol, Hyderabad 500007, India
来源：
CHEMPHOTOCHEM | 2025年
关键词：
1,7-enynes; diaryliodonium triflates; organo photoredox; cascade radical annulation and polydimethylsilox-ane (PDMS) microreactor; TRANSITION-METAL; DIARYLIODONIUM SALTS; PHENANTHRIDINONES; CYCLOISOMERIZATION; N-ENYNES; ANNULATION; ANALOGS; ACID; BOND;
D O I：
10.1002/cptc.202400332
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
We report an organophotoredox-catalyzed visible-light-induced tandem cyclization of 1,7-enynes with diaryliodoniumtriflates has been established leading to Phenanthridin-6(5H)-one derivatives under metal-free conditions. This transformation is initiated by visible light induced aryl radical formation from diaryliodoniumtriflates, followed by its regioseletive addition to the acrylate moiety of 1,7-enynes then undergoes intramolecular 6-exo-dig cascade radical annulation and which is terminated by single electron oxidation along with proton abstraction. This effective, sustainable and metal-free protocol exhibits a broad substrate scope and excellent tolerability towards various functional groups in good to excellent yields. Further implementation of a batch protocol to continuous flow protocol utilizing polydimethylsiloxane (PDMS) based microreactor exhibits its efficiency.
引用
收藏
页数：6
相关论文
共 25 条
  • [1] Copper-catalyzed cascade cyclization of 1,7-enynes with aromatic sulfonyl chlorides toward selective assembly of benzo[j]phenanthridin-6(5H)-ones
    Liu, Yu
    Zhang, Jia-Ling
    Zhou, Ming-Bo
    Song, Ren-Jie
    Li, Jin-Heng
    CHEMICAL COMMUNICATIONS, 2014, 50 (92) : 14412 - 14414
  • [2] Visible-Light-Induced Trifluoromethylation/Cyclization of 1,7-Enynes in Continuous Flow
    Zhuang, Kaiqiang
    Cui, Yusheng
    Yuan, Xin
    Qin, Longzhou
    Sun, Qi
    Duan, Xiu
    Chen, Lin
    Zhang, Xinpeng
    Qiu, Jiangkai
    Guo, Kai
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2020, 8 (31): : 11729 - 11736
  • [3] Synthesis of Fused Pyran Derivatives via Visible-Light-Induced Cascade Cyclization of 1,7-Enynes with Acyl Chlorides
    Li, Chen-Guang
    Xu, Guo-Qjang
    Xu, Peng-Fei
    ORGANIC LETTERS, 2017, 19 (03) : 512 - 515
  • [4] Visible-light-induced alkoxycarbonylation/cyclization of 1,7-enynes: synthesis of dihydropyranones containing all-carbon quaternary centers
    Chen, Jian-Qiang
    Chen, Qi
    Chen, Baofu
    Wu, Jie
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (08) : 2018 - 2023
  • [5] Visible-light-induced methylsulfonylation/bicyclization of C(sp3)-tethered 1,7-enynes using a DMSO/H2O system
    Huang, Min-Hua
    Zhu, Chi-Fan
    He, Chun-Lan
    Zhu, Yi-Long
    Hao, Wen-Juan
    Wang, De-Cai
    Tu, Shu-Jiang
    Jiang, Bo
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (10): : 1643 - 1650
  • [6] Visible-light-induced cascade radical cyclization to access sulfamoylated benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-ones
    Huang, Rong
    Wang, Wenbo
    Lu, Kui
    Zhao, Xia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2025, 23 (04) : 892 - 899
  • [7] Visible-Light-Induced Radical Cascade Cyclizations of 1,7-Enynes with Sulfinic Acids: Direct Access to Sulfonated Chromanes and Sulfonated Tetrahydroquinolines under Metal-Free Conditions
    Liu, Qi
    Mei, Yousheng
    Wang, Lei
    Ma, Yongmin
    Li, Pinhua
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (24) : 5669 - 5680
  • [8] Visible-light-induced radical-cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole: Access to benzoimidazo[2,1-a] isoquinolin-6(5H)-ones
    Wang, Yanhong
    Zhou, Xinlei
    Zhang, Tao
    Ren, Xinxin
    Xu, Wei
    Wang, Bin
    Jin, Weiwei
    Xia, Yu
    Liu, Chenjiang
    Zhang, Yonghong
    GREEN SYNTHESIS AND CATALYSIS, 2024, 5 (04): : 319 - 323
  • [9] Sulfur Incorporation: Copper-Catalyzed Cascade Cyclization of 1,7-Enynes with Metal Sulfides toward Thieno[3,4-c]quinolin-4(5H)-ones
    Liu, Yu
    Zhang, Jia-Ling
    Song, Ren-Jie
    Li, Jin-Heng
    ORGANIC LETTERS, 2014, 16 (22) : 5838 - 5841
  • [10] Visible light photoredox-catalyzed arylative cyclization to access benzimidazo[2,1-a]isoquinolin-6(5H)-ones
    Meher, Prahallad
    Samanta, Raj Kumar
    Manna, Sourav
    Murarka, Sandip
    CHEMICAL COMMUNICATIONS, 2023, 59 (40) : 6092 - 6095
123