Palladium-Catalyzed Double Carbonylation Reactions of o-Dihaloarenes with Amines in Phosphonium Salt Ionic Liquids

被引：66
作者：
Cao, Hong [1 ]
Alper, Howard [1 ]
机构：
[1] Univ Ottawa, Dept Chem, Ctr Catalysis Res & Innovat, Ottawa, ON K1N 6N5, Canada
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 18期
基金：
加拿大自然科学与工程研究理事会;
关键词：
PHTHALIMIDE DERIVATIVES; INTRAMOLECULAR CARBONYLATION; ENANTIOSELECTIVE SYNTHESIS; COMPLEXED DENDRIMERS; ARYL HALIDES; CYCLOCARBONYLATION; SEQUENCE; SILICA; THIOLS;
D O I：
10.1021/ol101714p
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Palladium-catalyzed double carbonylation of o-dihaloarenes with amines in phosphonium salt ionic liquids proceeds efficiently to give the corresponding N-substituted phthalimides. This process can tolerate a wide array of functional groups and affords products in excellent yields. The recyclability of the catalytic system was also investigated.
引用
收藏
页码：4126 / 4129
页数：4
相关论文
共 39 条
  • [1] Synthesis and anticonvulsant evaluation of N-substituted-isoindolinedione derivatives
    Abdel-Hafez, AAM
    [J]. ARCHIVES OF PHARMACAL RESEARCH, 2004, 27 (05) : 495 - 501
  • [2] New phthalimide derivatives with potent analgesic activity: II
    Antunes, R
    Batista, H
    Srivastava, RM
    Thomas, G
    Araujo, CC
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (21) : 3071 - 3076
  • [3] Microwave-induced one-pot synthesis of N-carboxyalkyl maleimides and phthalimides
    Borah, HN
    Boruah, RC
    Sandhu, JS
    [J]. JOURNAL OF CHEMICAL RESEARCH-S, 1998, (05): : 272 - +
  • [4] Industrial preparation of phosphonium ionic liquids
    Bradaric, CJ
    Downard, A
    Kennedy, C
    Robertson, AJ
    Zhou, YH
    [J]. GREEN CHEMISTRY, 2003, 5 (02) : 143 - 152
  • [5] Syntheses of Substituted 3-Methyleneisoindolin-1-ones By a Palladium-Catalyzed Sonogashira Coupling-Carbonylation-Hydroamination Sequence in Phosphonium Salt-Based Ionic liquids
    Cao, Hong
    McNamee, Laura
    Alper, Howard
    [J]. ORGANIC LETTERS, 2008, 10 (22) : 5281 - 5284
  • [6] Palladium-catalyzed thiocarbonylation of iodoarenes with thiols in phosphonium salt ionic liquids
    Cao, Hong
    McNamee, Laura
    Alper, Howard
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09) : 3530 - 3534
  • [7] Double carbonylation reactions of enynols and thiols to form thioester substituted 6-membered ring lactones
    Cao, Hong
    Xiao, Wen-Jing
    Alper, Howard
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (14) : 1807 - 1812
  • [8] New anti-inflammatory N-pyridinyl(alkyl)phthalimides acting as tumour necrosis factor-α production inhibitors
    Collin, X
    Robert, JM
    Wielgosz, G
    Le Baut, G
    Bobin-Dubigeon, C
    Grimaud, N
    Petit, JY
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2001, 36 (7-8) : 639 - 649
  • [9] Catalytic asymmetric cyclocarbonylation of o-isopropenylphenols:: Enantioselective synthesis of six-membered ring lactones
    Dong, C
    Alper, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) : 5011 - 5014
  • [10] Enantioselective cyclocarbonylation of 2-vinylanilines to six-membered ring lactams
    Dong, C
    Alper, H
    [J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (01) : 35 - 40
1234