Hydrogen transfer reduction of ketones using formic acid as a hydrogen donor under hydrothermal conditions

Journal of Zhejiang University: Science A

Volumn 10, Issue 11, 2009, Pages 1631-1635

  Shen, Zheng ^a   Jin, Fang Ming ^a   Zhang, Ya Lei ^a   Wu, Bing ^a   Cao, Jiang Lin ^a  

^a TONGJI UNIVERSITY   (China)

Author keywords

Formic acid; Hydrogen transfer reduction; Hydrothermal reaction; Ketone

Indexed keywords

HYDROGEN DONOR; HYDROGEN SOURCES; HYDROGEN-TRANSFER REDUCTION; HYDROTHERMAL CONDITIONS; HYDROTHERMAL REACTION; ISO-PROPANOLS; PYRUVIC ACID; WATER MOLECULE;

ACETONE; HYDROGEN; LACTIC ACID; ORGANIC ACIDS;

FORMIC ACID;

EID: 75649150765     PISSN: 1673565X     EISSN: 18621775     Source Type: Journal    
DOI: 10.1631/jzus.A0920097     Document Type: Article

References (23)

1. N. Akiya P.E. Savage 2002 The roles of water for chemical reactions in high-temperature water Chemical Reviews 102 8 2725 2750 10.1021/cr000668w (Pubitemid 35381647)
2. F. Alonso P. Riente M. Yus 2008 Hydrogen-transfer reduction of carbonyl compounds catalysed by nickel nanoparticles Tetrahedron Letters 49 12 1939 1942 10.1016/j.tetlet.2008.01.097 (Pubitemid 351258120)
3. F. Alonso P. Riente M. Yus 2008 Hydrogen-transfer reduction of carbonyl compounds promoted by nickel nanoparticles Tetrahedron 64 8 1847 1852 10.1016/j.tet.2007.11.093
4. E.J. Campbell H. Zhou S.T. Nguyen 2001 Catalytic Meerwein-Ponndorf-Verley reduction by simple aluminum complexes Organic Letters 3 15 2391 2393 10.1021/ol0162116 (Pubitemid 33629513)
5. E.J. Creyghton S.D. Ganeshie R.S. Downing H. van Bekkum 1997 Stereoselective Meerwein-Ponndorf-Verley and oppenauer reactions catalysed by zeolite BEA Journal of Molecular Catalysis A: Chemical 115 3 457 472 10.1016/S1381-1169(96)00351-2 (Pubitemid 27114753)
6. C.F. de Graauw J.A. Peters H. van Bekkum J. Huskens 1994 Meerwein-Ponndorf-Verley reductions and oppenauer oxidations: an integrated approach Synthesis 1994 10 1007 1017 10.1055/s-1994-25625
7. J. Ekström J. Wettergren H. Adolfsson 2007 A simple and efficient catalytic method for the reduction of ketones Advanced Synthesis & Catalysis 349 10 1609 1613 10.1002/adsc.200700091
8. A. Fujii S. Hashiguchi N. Uematsu T. Ikariya R. Noyori 1996 Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture Journal of the American Chemical Society 118 10 2521 2522 10.1021/ja954126l (Pubitemid 26120941)
9. 2 in supercritical water The Journal of Supercritical Fluids 19 3 251 262 10.1016/S0896-8446(00)00094-2 (Pubitemid 32246418)
10. F.M. Jin Z. Zhou H. Enomoto T. Moriya H. Higashijima 2004 Conversion mechanism of cellulosic biomass to lactic acid in subcritical water and acid-base catalytic effect of subcritical water Chemistry Letters 33 2 126 127 10.1246/cl.2004.126 (Pubitemid 38526406)
11. F.M. Jin J. Yun G.M. Li A. Kishita K. Tohji H. Enomoto 2008 Hydrothermal conversion of carbohydrate biomass into formic acid at mild temperatures Green Chemistry 10 6 612 615 10.1039/b802076k (Pubitemid 351782877)
12. B. Kuhlmann E.M. Arnett M. Siskin 1994 Classical or ganic reactions in pure superheated water The Journal of Organic Chemistry 59 11 3098 3101 10.1021/jo00090a030
13. Larock, R.C., 1989. Comprehensive Organic Transformation. VCH Publication, New York, p.35-39.
14. C. Li I. Yamai Y. Murase E. Kato 1989 Formation of acicular monoclinic zirconia particles under hydrothermal conditions Journal of the American Ceramic Society 72 8 1479 1482 10.1111/j.1151-2916.1989.tb07681.x
15. D.S. Matharu D.J. Morris G.J. Clarkson M. Wills 2006 An outstanding catalyst for asymmetric transfer hydrogenation in aqueous solution and formic acid/triethylamine Chemical Communications 30 3232 3234 10.1039/b606288a (Pubitemid 44126576)
16. H. Meerwein R. Schmidt 1925 Ein neues verfahren zur reaktion von aldehyden und ketonen Justus Liebigs Annalen der Chemie 444 1 221 238 10.1002/jlac.19254440112
17. S. Naskar M. Bhattacharjee 2007 Regiospecific solvent-free transfer hydrogenation of α, β-unsaturated carbonyl compounds catalyzed by a cationic ruthenium(II) compound Tetrahedron Letters 48 3 465 467 10.1016/j.tetlet.2006.11.063 (Pubitemid 44894494)
18. W. Ponndorf 1926 Der reversible austausch der oxydationsstufen zwischen aldehyden oder ketonen einerseits und primären oder sekundären alkoholen anderseits Zeitschrift für Angewandte Chemie 39 5 138 143 10.1002/ange.19260390504
19. J.R. Ruiz C. Jiménez-Sanchidriána J.M. Hidalgoa 2007 Meerwein-Ponndorf-Verley reaction of acetophenones with 2-propanol over MgAl mixed oxide: the substituent effect Catalysis Communications 8 7 1036 1040 10.1016/j.catcom.2006.10.007 (Pubitemid 46729677)
20. R.W. Shaw Y.B. Brill A.A. Clifford C.A. Eckert E.U. Franck 1991 Supercritical water a medium for chemistry Chemical Engineering News 69 51 26 39
21. R.A. Sheldon 1994 Consider the environmental quotient ChemTech 24 3 38 47
22. Y. Tsujino C. Wakai N. Matubayasi M. Nakahara 1999 Noncatalytic cannizzaro-type reaction of formaldehyde in hot water Chemistry Letters 28 4 287 288 10.1246/cl.1999.287
23. M. Watanabe T. Sato H. Inomata R.L. Smith K. Arai A. Kruse E. Dinjus 2004 Chemical reactions of C1 compounds in near-critical and supercritical water Chemical Reviews 104 12 5803 5822 10.1021/cr020415y (Pubitemid 40025730)