Synthesis of Dihydrophosphaisocoumarins through a Palladium-Catalyzed Oxidative Cyclization of Arylphosphonic Acid Monoethyl Esters with 1,3-Dienes

被引:21
|
作者
Son, Jeong-Yu [1 ]
Kim, Hyunseok [1 ]
Jeon, Woo Hyung [1 ]
Baek, Yonghyeon [1 ]
Seo, Boram [1 ]
Um, Kyusik [1 ]
Lee, Kooyeon [2 ]
Lee, Phil Ho [1 ]
机构
[1] Kangwon Natl Univ, Dept Chem, Chunchon 24341, South Korea
[2] Kangwon Natl Univ, Dept Bio Hlth Technol, Chunchon 24341, South Korea
基金
新加坡国家研究基金会;
关键词
catalysis; C-H activation; cyclization; palladium; phosphaheterocycles; BOND-CLEAVAGE; PHOSPHAISOCOUMARINS; ACTIVATION; AZOBENZENES; MONOESTERS; DERIVATIVES; PHOSPHATES; AMIDATION; LIGANDS;
D O I
10.1002/adsc.201700742
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
An efficient synthetic method for the selective preparation of dihydrophosphaisocoumarins and their derivatives was developed through a palladium-catalyzed oxidative cyclization reaction of a wide range of arylphosphonic acid monoethyl esters with activated and unactivated 1,3-dienes, including 1-aryl-substituted 1,3-dienes and 1-alkyl-substituted 1,3-dienes, thus opening a new avenue for the synthesis of phosphaheterocyclic compounds.
引用
收藏
页码:3194 / 3206
页数:13
相关论文
共 50 条
  • [41] Photoinduced, Palladium-Catalyzed Enantioselective 1,2-Alkylsulfonylation of 1,3-Dienes
    Liu, Zhi-Lin
    Ye, Zhi-Peng
    Liao, Zi-hao
    Lu, Wei-Dong
    Guan, Jian-Ping
    Gao, Zi-Yi
    Chen, Kai
    Chen, Xiao-Qing
    Xiang, Hao-Yue
    Yang, Hua
    ACS CATALYSIS, 2024, 14 (05) : 3725 - 3732
  • [42] STEREOSELECTIVE AND REGIOSELECTIVE PALLADIUM-CATALYZED 1,4-DIACETOXYLATION OF 1,3-DIENES
    BACKVALL, JE
    BYSTROM, SE
    NORDBERG, RE
    JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (24): : 4619 - 4631
  • [43] Palladium-catalyzed 1,2-selective intermolecular arylamination of 1,3-dienes
    Li, Zhuo-Mei
    Zhang, Zhe
    Li, Xue-Song
    Jiao, Rui-Qiang
    Chen, Xi
    Liu, Xue-Yuan
    ORGANIC CHEMISTRY FRONTIERS, 2024, : 6200 - 6206
  • [44] Stereoselective synthesis of benzofulvenes via a palladium-catalyzed cyclization of 1,3-dienes derived from Morita-Baylis-Hillman adducts
    Lim, Cheol Hee
    Kim, Ko Hoon
    Lim, Jin Woo
    Kim, Jae Nyoung
    TETRAHEDRON LETTERS, 2013, 54 (43) : 5808 - 5813
  • [45] Palladium-Catalyzed Oxidative Cross-Coupling of Conjugated Enynones with Allylarenes: Synthesis of Furyl-Substituted 1,3-Dienes
    Ping, Yifan
    Zhang, Sudong
    Chang, Taiwei
    Wang, Jianbo
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12): : 8275 - 8283
  • [46] Palladium-catalyzed synthesis of 3-trifluoromethylated 1,3-dienes from acrylate derivatives and BTP
    Zhao, Qun
    Wang, Jianjun
    Besset, Tatiana
    Pannecoucke, Xavier
    Bouillon, Jean-Philippe
    Poisson, Thomas
    TETRAHEDRON, 2018, 74 (41) : 6033 - 6040
  • [47] Efficient Palladium-Catalyzed Carbonylation of 1,3-Dienes: Selective Synthesis of Adipates and Other Aliphatic Diesters
    Yang, Ji
    Liu, Jiawang
    Ge, Yao
    Huang, Weiheng
    Ferretti, Francesco
    Neumann, Helfried
    Jiao, Haijun
    Franke, Robert
    Jackstell, Ralf
    Beller, Matthias
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (17) : 9527 - 9533
  • [48] Synthesis of Dihydrobenzofurans via Palladium-Catalyzed Annulation of 1,3-Dienes by o-Iodoaryl Acetates
    Rozhkov, Roman V.
    Larock, Richard C.
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (12): : 4131 - 4134
  • [49] Palladium-Catalyzed Proaromatic C(Alkenyl)-H Olefination: Synthesis of Densely Functionalized 1,3-Dienes
    Wang, Yu-Chun
    Huang, Yen-Hsiang
    Tsai, Hung-Chang
    Basha, R. Sidick
    Chou, Chih-Ming
    ORGANIC LETTERS, 2020, 22 (17) : 6765 - 6770
  • [50] PALLADIUM-CATALYZED OXIDATIVE CYCLIZATION OF 1,5-DIENES - A MECHANISTIC INVESTIGATION
    MOBERG, C
    SUTIN, L
    HEUMANN, A
    ACTA CHEMICA SCANDINAVICA, 1991, 45 (01): : 77 - 81