Facile synthesis of alkylphosphonates from 4-alkyl-1,4-dihydropyridines via photoinduced formal deformylative phosphonylation

被引:2
|
作者
Zhang, Huan [1 ]
Cui, Zhonghe [1 ]
Wang, Jian [2 ]
Zhu, Lin [2 ]
Li, Chaozhong [1 ,2 ]
机构
[1] ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Fluorine & Nitrogen Chem & Adv Mat, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 16期
基金
中国国家自然科学基金;
关键词
RADICAL TRAP; 1,4-DIHYDROPYRIDINES; ALKYLATION;
D O I
10.1039/d4qo00863d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Here, an unprecedented formal deformylative phosphonylation is disclosed. Under the catalysis of 1 mol% 1,2,3,5-tetrakis(diphenylamino)-4,6-dicyanobenzene (4DPAIPN) and in the presence of 200 mol% triethylamine as an additive, 4-alkyl-1,4-dihydropyridines (DHPs), derived from aldehydes, smoothly underwent phosphonylation with 9-fluorenyl o-phenylene phosphite, allowing facile synthesis of alkylphosphonates. This strategy is applicable to primary, secondary, and even tertiary DHPs and exhibits a broad substrate scope and excellent functional group tolerance, thereby enabling the late-stage phosphonylation of a series of naturally-occurring bioactive and biorelevant molecules.
引用
收藏
页码:4502 / 4507
页数:6
相关论文
共 50 条
  • [21] Photoredox- and Nickel-Catalyzed Hydroalkylation of Alkynes with 4-Alkyl-1,4-dihydropyridines: Ligand-Controlled Regioselectivity
    Zhang, Yulin
    Tanabe, Yoshiaki
    Kuriyama, Shogo
    Nishibayashi, Yoshiaki
    CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (36)
  • [22] Iron-Promoted Oxidative Alkylation/Cyclization of Ynones with 4-Alkyl-1,4-dihydropyridines: Access to 2-Alkylated Indenones
    Xiong, Fang-Ting
    He, Bin-Hong
    Liu, Yu
    Zhou, Quan
    Fan, Jian-Hong
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (13): : 8599 - 8610
  • [23] Radical-Based C-C Bond-Forming Processes Enabled by the Photoexcitation of 4-Alkyl-1,4-dihydropyridines
    Buzzetti, Luca
    Prieto, Alexis
    Roy, Sudipta Raha
    Melchiorre, Paolo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (47) : 15039 - 15043
  • [24] UNUSUAL OXIDATIVE DEALKYLATION OF CERTAIN 4-ALKYL-1,4-DIHYDROPYRIDINES WITH MNO2/BENTONITE USING MICROWAVE IRRADIATION, IN THE ABSENCE OF SOLVENT(II)
    DELGADO, F
    ALVAREZ, C
    GARCIA, O
    PENIERES, G
    MARQUEZ, C
    SYNTHETIC COMMUNICATIONS, 1991, 21 (21) : 2137 - 2141
  • [25] Copper-promoted cross-coupling of nitroarenes with 4-alkyl-1,4-dihydropyridines using a peroxide-driven radical reductive strategy
    Jiang, Hui-Min
    Qin, Jing-Hao
    Sun, Qing
    Zhang, Dong
    Jiang, Jin-Peng
    Ouyang, Xuan-Hui
    Song, Ren-Jie
    Li, Jin-Heng
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (15) : 4070 - 4077
  • [26] Facile synthesis of isoxazole 4-and 5-carbaldehydes and their conversion to isoxazolyl-1,4-dihydropyridines
    Mirzaei, YR
    Bavili-Tabrizi, S
    Hashemi-Gohare, M
    Zare-Neirizi, H
    Edjlali, L
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2003, 35 (02) : 207 - 214
  • [27] Visible-light-mediated minisci C-H alkylation of heteroarenes with 4-alkyl-1,4-dihydropyridines using O2as an oxidant
    Dong, Jianyang
    Yue, Fuyang
    Xu, Wentao
    Song, Hongjian
    Liu, Yuxiu
    Wang, Qingmin
    GREEN CHEMISTRY, 2020, 22 (17) : 5599 - 5604
  • [28] ASYMMETRIC-SYNTHESIS OF 4-ALKYL-3,5-DIALKOXYCARBONYL-2,6-DIMETHYL-1,4-DIHYDROPYRIDINES
    MARTIN, N
    MARTINEZGRAU, A
    SEOANE, C
    MARCO, JL
    ALBERT, A
    CANO, FH
    TETRAHEDRON-ASYMMETRY, 1995, 6 (04) : 877 - 880
  • [29] Visible-Light-Mediated Aromatic Substitution Reactions of Cyanoarenes with 4-Alkyl-1,4-dihydropyridines through Double Carbon-Carbon Bond Cleavage
    Nakajima, Kazunari
    Nojima, Sunao
    Sakata, Ken
    Nishibayashi, Yoshiaki
    CHEMCATCHEM, 2016, 8 (06) : 1028 - 1032
  • [30] Visible-Light-Promoted Cross-Coupling Reactions of 4-Alkyl-1,4-dihydropyridines with Thiosulfonate or Selenium Sulfonate: A Unified Approach to Sulfides, Selenides, and Sulfoxides
    Li, Jian
    Yang, Xin-Er
    Wang, Shan-Le
    Zhang, Long-Long
    Zhou, Xiao-Zhou
    Wang, Shun-Yi
    Ji, Shun-Jun
    ORGANIC LETTERS, 2020, 22 (12) : 4908 - 4913