Palladium catalyzed activation of borane–amine adducts: rate enhancement of amine–borane methanolysis in the reduction of nitrobenzenes to anilines
作者： Michel Couturier , John L Tucker , Brian M Andresen , Pascal Dubé , Steven J Brenek
DOI: 10.1016/S0040-4039(01)00166-6
关键词:
摘要: Abstract 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, catalyzed methanolysis/decomplexation borane–amine adducts accelerated by action nitrobenzene.
elsevier.com
sci-hub.se 参考文章(41)
YASUO KIKUGAWA, YOSHIE OGAWA, Chemistry of Amine-Boranes. VIII. Reduction of Aldehydes and Ketones with Pyridine-Borane in Trifluoroacetic Acid Chemical & Pharmaceutical Bulletin. ,vol. 27, pp. 2405- 2410 ,(1979) , 10.1248/CPB.27.2405
Yasuo Kikugawa, Masami Kawase, SELECTIVE REDUCTION OF OXIMES WITH PYRIDINE-BORANE Chemistry Letters. ,vol. 6, pp. 1279- 1280 ,(1977) , 10.1246/CL.1977.1279
Eckehard V. Dehmlow, Thomas Niemann, Anke Kraft, Mild and Fast Deoxygenation of Aromatic Carbonyl Compounds by Dimethylamine Borane / Titanium Tetrachloride Synthetic Communications. ,vol. 26, pp. 1467- 1472 ,(1996) , 10.1080/00397919608003512
Xing W-K, Ogata Y, ニトロベンゼンの含水エタノール中での塩化すず(II)還元のオルト置換基による立体加速 Journal of Organic Chemistry. ,vol. 47, pp. 3577- 3581 ,(1982)
John A. Soderquist, Ramon Huertas, Jesus R. Medina, MONO- AND DIALKYLBORANE REAGENTS FROM SILYLAMINE-BORANES Tetrahedron Letters. ,vol. 39, pp. 6123- 6126 ,(1998) , 10.1016/S0040-4039(98)01262-3
John A. Soderquist, Jesus R. Medina, Ramon Huertas, Novel hydroborating agents from silylamine-boranes Tetrahedron Letters. ,vol. 39, pp. 6119- 6122 ,(1998) , 10.1016/S0040-4039(98)01261-1
G.C. Andrews, T.C. Crawford, The synthetic utility of amine borane reagents in the reduction of aldehydes and ketones Tetrahedron Letters. ,vol. 21, pp. 693- 696 ,(1980) , 10.1016/S0040-4039(00)71448-1
Herbert C. Brown, Josyula V. B. Kanth, Pramod V. Dalvi, Marek Zaidlewicz, Molecular addition compounds. 16. New, highly reactive borane adducts with N,N-dialkyl-tert-alkylamines for hydroboration Journal of Organic Chemistry. ,vol. 65, pp. 4655- 4661 ,(2000) , 10.1021/JO0002745
F.D. Bellamy, K. Ou, Selective reduction of aromatic nitro compounds with stannous chloride in non acidic and non aqueous medium Tetrahedron Letters. ,vol. 25, pp. 839- 842 ,(1984) , 10.1016/S0040-4039(01)80041-1
D. Channe Gowda, A. S. Prakasha Gowda, A. Ramesha Baba, Shankare Gowda, Nickel-Catalyzed Formic Acid Reductions. A Selective Method for the Reduction of Nitro Compounds Synthetic Communications. ,vol. 30, pp. 2889- 2895 ,(2000) , 10.1080/00397910008087439