Palladium-catalyzed decarboxylation and decarbonylation under hydrothermal conditions: Decarboxylative deuteration

被引:119
作者
Matsubara, S [1 ]
Yokota, Y [1 ]
Oshima, K [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6158510, Japan
关键词
D O I
10.1021/ol0492602
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Decarboxylation of free carboxylic acid was performed by Pd/C catalyst under hydrothermal water (250 degreesC/4 MPa). Under the hydrothermal conditions of deuterium oxide, decarbonylative deuteration was observed to give fully deuterated hydrocarbons from carboxylic acids or aldehydes.
引用
收藏
页码:2071 / 2073
页数:3
相关论文
共 33 条
[1]   Roles of water for chemical reactions in high-temperature water [J].
Akiya, N ;
Savage, PE .
CHEMICAL REVIEWS, 2002, 102 (08) :2725-2750
[2]   Applications of high-temperature aqueous media for synthetic organic reactions [J].
An, JY ;
Bagnell, L ;
Cablewski, T ;
Strauss, CR ;
Trainor, RW .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2505-2511
[3]   NUCLEAR MAGNETIC RESONANCE SPECTRA AND CONFORMATIONS OF DEUTERATED CYCLOOCTANES [J].
ANET, FAL ;
STJACQUE.M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (11) :2585-&
[4]   A SIMPLIFIED PREPARATION OF FULLY DEUTERATED HIGH MOLECULAR WEIGHT HYDROCARBONS [J].
ATKINSON, JG ;
LUKE, MO ;
STUART, RS .
CANADIAN JOURNAL OF CHEMISTRY, 1967, 45 (13) :1511-&
[5]   Microwave-enhanced metal- and acid-catalysed hydrogen isotope exchange reactions [J].
Barthez, JM ;
Filikov, AV ;
Frederiksen, LB ;
Huguet, ML ;
Jones, JR ;
Lu, SY .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1998, 76 (06) :726-728
[6]  
Bröll D, 1999, ANGEW CHEM INT EDIT, V38, P2999
[7]   The ruthenium-catalyzed reductive decarboxylation of esters: Catalytic reactions involving the cleavage of acyl-oxygen bonds of esters [J].
Chatani, N ;
Tatamidani, H ;
Ie, Y ;
Kakiuchi, F ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (20) :4849-4850
[8]   The activation barrier to axial torsion in 2,2'-bis(diphenylphosphino)biphenyl [J].
Desponds, O ;
Schlosser, M .
TETRAHEDRON LETTERS, 1996, 37 (01) :47-48
[9]   Deuterium exchange mediated by an iridium-phosphine complex formed in situ [J].
Ellames, GJ ;
Gibson, JS ;
Herbert, JM ;
Kerr, WJ ;
McNeill, AH .
TETRAHEDRON LETTERS, 2001, 42 (36) :6413-6416
[10]   Microwave-assisted deuterium exchange reactions for the preparation of reactive intermediates [J].
Fodor-Csorba, K ;
Galli, G ;
Holly, S ;
Gäcs-Baitz, E .
TETRAHEDRON LETTERS, 2002, 43 (21) :3789-3792