Pd(II)-Catalyzed Synthesis of Alkylidene Phthalides via a Decarbonylative Annulation Reaction

被引:23
|
作者
Borthakur, Somadrita [1 ]
Baruah, Swagata [1 ]
Sarma, Bipul [2 ]
Gogoi, Sanjib [1 ]
机构
[1] CSIR North East Inst Sci & Technol, Appl Organ Chem Chem Sci & Technol Div, AcSIR, Jorhat 785006, Assam, India
[2] Tezpur Univ, Dept Chem Sci, Tezpur 784028, India
关键词
GAMMA-BUTYROLACTONES; EFFICIENT APPROACH; FREDERICAMYCIN-A; LACTONES; CLEAVAGE;
D O I
10.1021/acs.orglett.9b00726
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An unprecedented Pd(II)-catalyzed decarbonylative C-H/C-C activation and annulation reaction, which proceeds via intramolecular cyclization, is reported. This reaction of hydroxynaphthoquinones with disubstituted alkynes provides good yields of substituted alkylidene phthalides, which are the key intermediates for the synthesis of bioactive natural products.
引用
收藏
页码:2768 / 2771
页数:4
相关论文
共 50 条
  • [1] Ru(ii)-Catalyzed cascade decarbonylative annulation and dehydrogenative alkenylation reactions: synthesis of phthalides†
    Baruah, Swagata
    Sultana, Sabera
    Bhorali, Pratiksha
    Saikia, Pallabi
    Gogoi, Sanjib
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (13) : 2997 - 3003
  • [2] Ru(ii)-Catalyzed cascade decarbonylative annulation and dehydrogenative alkenylation reactions: synthesis of phthalides
    Baruah, Swagata
    Sultana, Sabera
    Bhorali, Pratiksha
    Saikia, Pallabi
    Gogoi, Sanjib
    Organic and Biomolecular Chemistry, 2021, 19 (13): : 2997 - 3003
  • [3] Ruthenium(II)-Catalyzed Synthesis of Spirobenzofuranones by a Decarbonylative Annulation Reaction
    Kaishap, Partha P.
    Duarah, Gauri
    Sarma, Bipul
    Chetia, Dipak
    Gogoi, Sanjib
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (02) : 456 - 460
  • [4] A Pd(<sc>ii</sc>)-catalyzed denitrative alkyne annulation reaction for the synthesis of cyclopenta[b]chromanes
    Bhorali, Pratiksha
    Kalita, Deep J.
    Das, Babulal
    Gogoi, Sanjib
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (10) : 2834 - 2838
  • [5] Facile Synthesis of Alkylidene Phthalides by Rhodium-Catalyzed Domino C-H Acylation/Annulation of Benzamides with Aliphatic Carboxylic Acids
    Liu, Sien
    He, Bangyue
    Li, Hongyi
    Zhang, Xiaofeng
    Shang, Yaping
    Su, Weiping
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (63) : 15628 - 15633
  • [6] Synthesis of meso-5-azaindolyl-appended Zn(II) porphyrins via Pd-catalyzed annulation
    Maeda, Chihiro
    Shinokubo, Hiroshi
    Osuka, Atsuhiro
    ORGANIC LETTERS, 2007, 9 (13) : 2493 - 2496
  • [7] Streamlined synthesis of phenylene-containing PAHs via Pd catalyzed annulation
    Xia, Yan
    Teo, YewChin
    Jin, Zexin
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [8] Pd-Catalyzed Asymmetric Dearomatization of Indoles via Decarbonylative Heck-Type Reaction of Thioesters
    Han, Ming-Liang
    Huang, Wei
    Liu, Yu-Wen
    Liu, Min
    Xu, Hui
    Xiong, Hai
    Dai, Hui-Xiong
    ORGANIC LETTERS, 2021, 23 (01) : 172 - 177
  • [9] Decarbonylative Issues Involved in Ru(II)-catalyzed [6+2-1] Annulation Reaction of Hydroxychromone with Alkyne: A DFT Study
    Ling, Baoping
    Wang, Jiarong
    Liu, Yuxia
    Jiang, Yuan-Ye
    Liu, Peng
    Feng, Jin
    Bi, Siwei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (02) : 266 - 273
  • [10] Modular Synthesis of Benzocyclobutenes via Pd(II)-Catalyzed Oxidative [2+2] Annulation of Arylboronic Acids with Alkenes
    Fujii, Takuji
    Gallarati, Simone
    Corminboeuf, Clemence
    Wang, Qian
    Zhu, Jieping
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (20) : 8920 - 8926