Heteroaromatic benzyl ethers as intermediates for palladium-catalysed transfer hydrogenolysis of benzyl alcohols

被引：32
作者：
Araújo, NCP [1 ]
Brigas, AF [1 ]
Cristiano, MLS [1 ]
Frija, LMT [1 ]
Guimaraes, EMO [1 ]
Loureiro, RMS [1 ]
机构：
[1] Univ Algarve, Fac Ciencias & Tecnol, Dept Quim & Bioquim, Ctr Invest Quim & Catalise, P-8005039 Faro, Portugal
来源：
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2004年 / 215卷 / 1-2期
关键词：
palladium-on-charcoal; transfer hydrogenolysis; tetrazoles; benzisothiazoles;
D O I：
10.1016/j.molcata.2003.12.033
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：
A chemoselective and easy to carry procedure for the hydrogenolysis of benzyl alcohols is described. Benzyl alcohols are readily converted into tetrazolyl and benzisothiazolyl ethers that can be catalytically hydrogenolysed to toluenes over palladium-on-charcoal using hydrogen donors. The effect of electronwithdrawing heteroaromatic substituents is interpreted on the basis of chrystallographic structure determinations and molecular orbital calculations. (C) 2004 Elsevier B.V. All rights reserved.
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收藏
页码：113 / 120
页数：8
相关论文
共 35 条
[1]   TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].
ALLEN, FH ;
KENNARD, O ;
WATSON, DG ;
BRAMMER, L ;
ORPEN, AG ;
TAYLOR, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19
[2]   Metal-assisted reactions .26. Catalytic reactivity and ether bond lengths in aryloxytetrazoles and aryloxypseudosaccharins [J].
Alves, JAC ;
Barkley, JV ;
Brigas, AF ;
Johnstone, RAW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (04) :669-677
[3]   Metal-assisted reactions. Part XXX. Control of rates of heterogeneously catalyzed transfer hydrogenolysis through changes in solvent composition [J].
Alves, JAC ;
Brigas, AF ;
Johnstone, RAW .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2003, 56 (05) :423-428
[4]   Structural effects on sigmatropic shifts in heteroaromatic allyl ethers [J].
Araújo, NCP ;
Barroca, PMM ;
Bickley, JF ;
Brigas, AF ;
Cristiano, MLS ;
Johnstone, RAW ;
Loureiro, RMS ;
Pena, PCA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (09) :1213-1219
[5]  
Augustine R.L., 1996, HETEROGENEOUS CATALY
[6]   3-(E)-but-2-enoxy-1,2-benzisothiazole 1,1-dioxide: Unusual C-O-C ether bond lengths and reactivity [J].
Barkley, JV ;
Cristiano, MLS ;
Johnstone, RAW ;
Loureiro, RMS .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1997, 53 :383-386
[7]   DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR [J].
BECKE, AD .
PHYSICAL REVIEW A, 1988, 38 (06) :3098-3100
[8]  
Boudart M., 2014, KINETICS HETEROGENEO
[9]   4-Quinolylmethyl and 1-naphthylmethyl as benzyl-type protecting groups of carboxylic acids removable by homogeneous palladium-catalyzed hydrogenolysis [J].
Boutros, A ;
Legros, JY ;
Fiaud, JC .
TETRAHEDRON, 2000, 56 (15) :2239-2246
[10]   MILD HYDROGEN-TRANSFER REDUCTIONS USING SODIUM HYPOPHOSPHITE [J].
BOYER, SK ;
BACH, J ;
MCKENNA, J ;
JAGDMANN, E .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (18) :3408-3411
1234