Palladium-catalyzed carbonylative synthesis of isocoumarins and phthalides by using phenyl formate as a carbon monoxide source

被引:21
|
作者
Yuan, Qing [1 ]
Chen, Zhen-Bang [1 ]
Zhang, Fang-Ling [1 ]
Zhu, Yong-Ming [1 ]
机构
[1] Soochow Univ, Coll Pharmaceut Sci, Suzhou 215123, Peoples R China
关键词
3-SUBSTITUTED ISOCOUMARINS; COUPLING REACTIONS; THUNBERGINOL-B; ALPHA-PYRONES; ARYL HALIDES; ACID; CYCLIZATION; ALKYNES; 3-YLIDENEPHTHALIDES; DERIVATIVES;
D O I
10.1039/c6ob02409b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and efficient palladium-catalyzed intramolecular carbonylative synthesis of isocoumarins and phthalides from the easily available starting materials by employing phenyl formate as a CO surrogate has been achieved. The approach affords target compounds in good to excellent yields with the advantages of lower toxicity, milder conditions, easy operation and wide functional group tolerance.
引用
收藏
页码:1628 / 1635
页数:8
相关论文
共 50 条
  • [1] Carbonylative Synthesis of Phthalimides and Benzoxazinones by Using Phenyl Formate as a Carbon Monoxide Source
    Chavan, Sujit P.
    Bhanage, Bhalchandra M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (11) : 2405 - 2410
  • [2] Palladium-Catalyzed Carbonylative Synthesis of N-Benzoylindoles with Mo(CO)6 as the Carbon Monoxide Source
    Wu, Xiao-Feng
    Oschatz, Stefan
    Sharif, Muhammad
    Langer, Peter
    SYNTHESIS-STUTTGART, 2015, 47 (17): : 2641 - 2646
  • [3] Palladium Catalyzed Carbonylative Coupling for Synthesis of Arylketones and Arylesters Using Chloroform as the Carbon Monoxide Source
    Sharma, Poonam
    Rohilla, Sandeep
    Jain, Nidhi
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (02): : 1105 - 1113
  • [4] Palladium-Catalyzed Synthesis of Isocoumarins and Phthalides via tert-Butyl Isocyanide Insertion
    Fei, Xiang-Dong
    Ge, Zhi-Yuan
    Tang, Ting
    Zhu, Yong-Ming
    Ji, Shun-Jun
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22): : 10321 - 10328
  • [5] Palladium-Catalyzed Carbonylative Synthesis of Phthalimides from 1,2-Dibromoarenes with Molybdenum Hexacarbonyl as Carbon Monoxide Source
    Wu, Xiao-Feng
    Oschatz, Stefan
    Sharif, Muhammad
    Flader, Anika
    Krey, Lisa
    Beller, Matthias
    Langer, Peter
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (18) : 3581 - 3585
  • [6] Palladium-catalyzed carbonylative synthesis of indoloisoindoloquinazolinone derivatives by using CO as a carbonyl source
    Guo, Shenghai
    Wang, Fang
    Liu, Yangfan
    Fan, Xuesen
    TETRAHEDRON, 2019, 75 (24) : 3355 - 3360
  • [7] A Convenient Palladium-Catalyzed Carbonylative Suzuki Coupling of Aryl Halides with Formic Acid as the Carbon Monoxide Source
    Qi, Xinxin
    Jiang, Li-Bing
    Li, Hao-Peng
    Wu, Xiao-Feng
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (49) : 17650 - 17656
  • [8] Palladium-Catalyzed Carbonylative Synthesis of Heterocycles
    Feng, Jian-Bo
    Wu, Xiao-Feng
    HETEROCYCLIC CHEMISTRY IN THE 21ST CENTURY: A TRIBUTE TO ALAN KATRITZKY, 2017, 121 : 207 - 246
  • [9] Palladium-Catalyzed Carbonylative Synthesis of Benzogerminones
    Chen, Bo
    Wu, Xiao-Feng
    SYNLETT, 2019, 30 (13) : 1592 - 1596
  • [10] Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides Using Near Stoichiometric Carbon Monoxide
    Neumann, Karoline T.
    Laursen, Simon R.
    Lindhardt, Anders T.
    Bang-Andersen, Benny
    Skrydstrup, Troels
    ORGANIC LETTERS, 2014, 16 (08) : 2216 - 2219