Palladium catalyzed activation of borane-amine adducts:: rate enhancement of amine-borane methanolysis in the reduction of nitrobenzenes to anilines

被引:23
作者
Couturier, M [1 ]
Tucker, JL [1 ]
Andresen, BM [1 ]
Dubé, E [1 ]
Brenek, SJ [1 ]
Negri, JT [1 ]
机构
[1] Pfizer Global Res & Dev, Chem Res & Dev, Groton, CT 06340 USA
关键词
D O I
10.1016/S0040-4039(01)00166-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Hydrolytically stable borane-amines can be activated in situ through palladium catalysis and perform reductions not possible otherwise. Hence, borane-trimethylamine is an efficient hydrogen-transfer reagent for the open vessel reduction of nitroaryls to anilines. Likewise, the palladium catalyzed methanolysis/decomplexation of stable borane-amine adducts is accelerated by the action of nitrobenzene. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2285 / 2288
页数:4
相关论文
共 45 条
[1]   SYNTHETIC UTILITY OF AMINE BORANE REAGENTS IN THE REDUCTION OF ALDEHYDES AND KETONES [J].
ANDREWS, GC ;
CRAWFORD, TC .
TETRAHEDRON LETTERS, 1980, 21 (08) :693-696
[2]  
[Anonymous], ORG PREP PROCED INT
[3]   ENHANCED REDUCING PROPERTIES OF PYRIDINE BORANE ADSORBED ON SOLID SUPPORTS - A CONVENIENT METHOD FOR CHEMOSELECTIVE REDUCTION OF ALDEHYDES [J].
BABLER, JH ;
SARUSSI, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (23) :4416-4419
[4]   Chemoselective reduction of nitroaromatics to anilines using decaborane in methanol [J].
Bae, JW ;
Cho, YJ ;
Lee, SH ;
Yoon, CM .
TETRAHEDRON LETTERS, 2000, 41 (02) :175-177
[5]   Ultrasound-promoted highly efficient reduction of aromatic nitro compounds to the aromatic amines by samarium/ammonium chloride [J].
Basu, MK ;
Becker, FF ;
Banik, BK .
TETRAHEDRON LETTERS, 2000, 41 (30) :5603-5606
[6]  
BERGER JG, 1974, SYNTHESIS-STUTTGART, P508
[7]   REDUCTION OF SCHIFF BASES .3. REDUCTION WITH DIMETHYLAMINE BORANE [J].
BILLMAN, JH ;
MCDOWELL, JW .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (05) :1437-&
[8]  
BRAUDE EA, 1954, J CHEM SOC, P3856
[9]   Molecular addition compounds.: 11.: N-ethyl-N-isopropylaniline-borane, a superior reagent for hydroborations and reductions [J].
Brown, HC ;
Kanth, JVB ;
Zaidlewicz, M .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (15) :5154-5163
[10]   Molecular addition compounds. 10. Borane adducts with N,N-Dialkylanilines for hydroboration [J].
Brown, HC ;
Zaidlewicz, M ;
Dalvi, PV .
ORGANOMETALLICS, 1998, 17 (19) :4202-4205