Three-component Barbier allylation, Friedel-Crafts alkylation and intramolecular hydroalkoxylation in an ionic liquid for the direct synthesis of 4-arylchromans

被引：7
作者：
Zhao, Xian-Liang [1 ]
Liu, Li [1 ]
Chen, Yong-Jun [1 ]
Wang, Dong [1 ]
机构：
[1] Chinese Acad Sci, Inst Chem, Biol Chem Lab, BNLMS, Beijing 100080, Peoples R China
来源：
SYNLETT | 2007年 / 09期
关键词：
Barbier; Friedel-Crafts; hydroalkoxylation; one-pot process; 4-arylchroman; ionic liquid;
D O I：
10.1055/s-2007-980353
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
4-Arylchromans can be synthesized directly using a one-pot Barbier allylation, Friedel-Crafts alkylation and intramolecular hydroalkoxylation of aromatic aldehydes, allylbromides and phenols in an ionic liquid (BPyX-SnCl2 center dot 2H(2)O). The intramolecular hydroalkoxylation of 4-aryl-4-(2-hydroxylphenyl)but-1-enes can be promoted using the Lewis acid ZnCl2 in an ionic liquid.
引用
收藏
页码：1357 / 1364
页数：8
相关论文
共 46 条
  • [1] Intramolecular arylation reactions of alkenes:: A flexible approach to chromans and tetrahydroquinoline derivatives
    Barluenga, J
    Trincado, M
    Rubio, E
    González, JM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) : 3416 - 3417
  • [2] Rhodium(I)-catalyzed addition of phenols to dienes.: A new convergent synthesis of vitamin E
    Bienaymé, H
    Ancel, JE
    Meilland, P
    Simonato, JP
    [J]. TETRAHEDRON LETTERS, 2000, 41 (18) : 3339 - 3343
  • [3] SELECTIVITY IN REACTIONS BETWEEN METAL PHENOXIDES AND ISOPRENE - FACILE SYNTHESIS OF 2,2-DIMETHYLCHROMANS
    BOLZONI, L
    CASIRAGHI, G
    CASNATI, G
    SARTORI, G
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (09): : 684 - 686
  • [4] BROWERS WS, 1976, SCIENCE, V193, P542
  • [5] Asymmetric Mannich-type reactions catalyzed by indium(III) complexes in ionic liquids
    Chen, SL
    Ji, SJ
    Loh, TP
    [J]. TETRAHEDRON LETTERS, 2003, 44 (11) : 2405 - 2408
  • [6] Catalytic formation of C-O bonds by alkene activation:: Lewis acid-cycloisomerisation of olefinic alcohols
    Coulombel, L
    Favier, I
    Duñach, E
    [J]. CHEMICAL COMMUNICATIONS, 2005, (17) : 2286 - 2288
  • [7] Triflic acid-catalysed cyclisation of unsaturated alcohols
    Coulombel, L
    Duñach, E
    [J]. GREEN CHEMISTRY, 2004, 6 (10) : 499 - 501
  • [8] (+)-myristinins A and D from Knema elegans, which inhibit DNA polymerase β and cleave DNA
    Deng, JZ
    Starck, SR
    Li, SS
    Hecht, SM
    [J]. JOURNAL OF NATURAL PRODUCTS, 2005, 68 (11): : 1625 - 1628
  • [9] ELLIS GP, 1981, CHROMANES TOCOPHEROL
  • [10] Palladium(II)-catalyzed aerobic hydroalkoxylation of styrenes containing a phenol
    Gligorich, KM
    Schultz, MJ
    Sigman, MS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (09) : 2794 - 2795
12345