Palladium-catalyzed isomerization of (homo-)allylic alcohols in molten tetrabutylammonium bromide, a recyclable system

被引:32
作者
Ganchegui, B [1 ]
Bouquillon, S [1 ]
Hénin, F [1 ]
Muzart, J [1 ]
机构
[1] Univ Reims, CNRS, UMR React Select & Applicat, F-51687 Reims 2, France
关键词
palladium-catalysis; isomerization; (Homo-)allylic alcohols; Molten ammonium salt; recycling;
D O I
10.1016/j.molcata.2003.09.033
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Saturated ketones have been produced by heating secondary allylic alcohols and catalytic amounts of PdCl2 or Pd(OAc)(2) in molten n-Bu4NBr. After extraction of the organic material with diethyl ether, the ionic layer and the catalyst can be reused directly. Linear secondary homoallylic alcohols led also to the corresponding saturated ketones as main products. The procedure was less selective for primary allylic alcohols. (C) 2004 Elsevier B.V. All rights reserved.
引用
收藏
页码:65 / 69
页数:5
相关论文
共 39 条
  • [1] PALLADIUM(II)-MEDIATED OXIDATION OF ALCOHOLS USING 1,2-DICHLOROETHANE AS PD(0) REOXIDANT
    AITMOHAND, S
    HENIN, F
    MUZART, J
    [J]. TETRAHEDRON LETTERS, 1995, 36 (14) : 2473 - 2476
  • [2] Ruthenium-catalyzed Oppenauer-type oxidation of 3 beta-hydroxy steroids. A highly efficient entry into the steroidal hormones with 4-en-3-one functionality
    Almeida, MLS
    Kocovsky, P
    Backvall, JE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (19) : 6587 - 6590
  • [3] Heck arylation of allylic alcohols in molten salts
    Bouquillon, S
    Ganchegui, B
    Estrine, B
    Hénin, F
    Muzart, J
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 634 (02) : 153 - 156
  • [4] Theoretical study on the mechanism of iron carbonyls mediated isomerization of allylic alcohols to saturated carbonyls
    Branchadell, V
    Crévisy, C
    Grée, R
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (09) : 2062 - 2067
  • [5] CHAUVIN Y, 1995, CHEMTECH, V25, P26
  • [6] From curiosities to commodities: ionic liquids begin the transition
    Davis, JH
    Fox, PA
    [J]. CHEMICAL COMMUNICATIONS, 2003, (11) : 1209 - 1212
  • [7] de Bellefon C, 2000, ANGEW CHEM INT EDIT, V39, P3442, DOI 10.1002/1521-3773(20001002)39:19<3442::AID-ANIE3442>3.0.CO
  • [8] 2-Q
  • [9] Delaby R., 1926, CR HEBD ACAD SCI, V182, P140
  • [10] 2 FACTORS IN THERMAL CIS-TRANS REARRANGEMENT OF PENTAENES - CONFIGURATION IN (E,E)-OCTAHYDRO-2,2'-BI-3H-NAPHTHYLIDENE - EXTENSIVITY IN 2,2'-BICHOLESTADIENYLIDENES AND 3,3'-BICHOLESTADIENYLIDENES
    DOERING, WV
    BIRLADEANU, L
    CHENG, XH
    KITAGAWA, T
    SARMA, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (12) : 4558 - 4563