The Reductive Amination of Aldehydes and Ketones and the Hydrogenation of Nitriles: Mechanistic Aspects and Selectivity Control
This review deals with two of the most commonly used methods for the preparation of amines: the reductive amination of aldehydes and ketones and the hydrogenation of nitriles. There is a great similarity between these two methods, since both have the imine as intermediate. However, due to the high r...
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| Published in: | Advanced synthesis & catalysis Vol. 344; no. 10; pp. 1037 - 1057 |
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| Language: | English |
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WILEY-VCH Verlag
01.12.2002
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| ISSN: | 1615-4150, 1615-4169 |
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| Abstract | This review deals with two of the most commonly used methods for the preparation of amines: the reductive amination of aldehydes and ketones and the hydrogenation of nitriles. There is a great similarity between these two methods, since both have the imine as intermediate. However, due to the high reactivity of this intermediate, primary, secondary and/or tertiary amines are obtained (often simultaneously). The relation of the selectivity to different substrate structures and reaction conditions is briefly summarised, the main focus being on the catalyst as it is the most significant factor that governs the selectivity. Different mechanisms are discussed with the view to correlate the structure of the catalyst and, more particularly, the nature of the metal and the support with selectivity. The crucial point is the presumed location of the condensation and hydrogenation steps. |
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| AbstractList | This review deals with two of the most commonly used methods for the preparation of amines: the reductive amination of aldehydes and ketones and the hydrogenation of nitriles. There is a great similarity between these two methods, since both have the imine as intermediate. However, due to the high reactivity of this intermediate, primary, secondary and/or tertiary amines are obtained (often simultaneously). The relation of the selectivity to different substrate structures and reaction conditions is briefly summarised, the main focus being on the catalyst as it is the most significant factor that governs the selectivity. Different mechanisms are discussed with the view to correlate the structure of the catalyst and, more particularly, the nature of the metal and the support with selectivity. The crucial point is the presumed location of the condensation and hydrogenation steps. |
| Author | Peters, Joop A. Maschmeyer, Thomas Gomez, Silvia |
| Author_xml | – sequence: 1 givenname: Silvia surname: Gomez fullname: Gomez, Silvia organization: Laboratory of Applied Organic Chemistry and Catalysis, DelftChemTech, Delft University of Technology, Julianalaan 136, 2628 BL, Delft, The Netherlands Fax: (+31)-15-2781415 – sequence: 2 givenname: Joop A. surname: Peters fullname: Peters, Joop A. organization: Laboratory of Applied Organic Chemistry and Catalysis, DelftChemTech, Delft University of Technology, Julianalaan 136, 2628 BL, Delft, The Netherlands Fax: (+31)-15-2781415 – sequence: 3 givenname: Thomas surname: Maschmeyer fullname: Maschmeyer, Thomas email: Th.Maschmeyer@tnw.tudelft.nl organization: Laboratory of Applied Organic Chemistry and Catalysis, DelftChemTech, Delft University of Technology, Julianalaan 136, 2628 BL, Delft, The Netherlands Fax: (+31)-15-2781415 |
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61 Miller (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB40) 1940; 62 Carothers (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB45) 1925; 47 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB53A Malz, Jr. (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB9) 1991 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB53B Freifelder (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB5B) 1971 Hartung (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB38) 1928; 50 Bris (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB8B) 1964; 31 Emerson (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB5A) 1948 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB78 Freifelder (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB54) 1960; 82 Ranu (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB2C) 1998; 63 Birtill (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB12) 1998 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB76 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB70 Crowell (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB18) 1967; 32 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB52B 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB52C Greenfield (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB57) 1976; 15 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB52A Greenfield (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB97) 1994 Barney (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB3A) 1990; 31 Hückel (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB31) 1956; 89 Bonds (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB15B) 1992 Ikutani (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB33) 1969; 42 Devereux (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB98B) 1957 Winans (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB16A) 1933; 55 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB89 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB86 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB87 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB88 Schellenberg (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB2A) 1963; 28 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB82 Huang (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB94) 1999; 184 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB83 Göbölös (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB20) 1991 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB84 Volf (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB26) 1986 Gould (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB46) 1960; 25 Winans (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB77A) 1939; 61 Huang (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB95) 2000 Malz, Jr. (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB79A) 1992 Wallach (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB1B) 1905; 343 Leuckart (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB1A) 1885; 18 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB22A Galán (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB72) 1991; 56 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB22B Huang (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB60) 2000; 196 Gomez (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB49) Skita (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB30) 1929; 42 Mattocks (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB42A) 1948; 70 Archer (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB14) 1957; 79 Hochard (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB92) 1995; 95 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB90 Freifelder (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB34) 1971 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB91 Cabello (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB56) 1997; 167 Norton (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB16C) 1954; 19 Ogata (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB19) 1964; 29 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB22C Métayer (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB37) 1954 Dovell (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB75) 1965; 87 Cignarella (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB39) 1960; 82 Campbell (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB16B) 1944; 66 Grethe (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB77C) 1968; 33 Rode (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB81B) 1997; 148 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB28 Huang (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB81C) 1999; 182 Huber (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB51) 1944; 66 Peeling (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB98C) 1958 Alexander (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB43) 1948; 70 Blanchard (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB80A) 1991 Mallat (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB5G) 1997 Tichit (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB80D) 1997 Winans (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB47) 1939; 61 Rylander (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB5E) 1985 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB73I 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB73J 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB73G 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB73H Bris (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB8D) 1964; 31 Rylander (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB27) 1970; 11 Schwoegler (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB7) 1939; 61 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB73A 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB85B 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB73B 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB85A 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB73E 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB73F Freifelder (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB35) 1971 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB73C Pachter (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB10) 1960; 25 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB73D Bergeron (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB66) 1984 Surrey (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB77B) 1956; 78 Ashweek (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB3B) 2000; 41 Lehtonen (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB93) 1998; 2 Hamilton (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB98A) 1928; 50 Kindler (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB24) 1933; 271 Rylander (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB5C) 1979 Cope (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB74A) 1942; 64 Pasek (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB81A) 1981; 46 Scaros (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB79B) 1994 Iles (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB74B) 1961; 26 Dallons (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB80B) 1992 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB15A Malz, Jr. (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB21) 1994 Lochte (10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB36) 1948; 70 10.1002/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3-BIB79C Gomez (10.1002/1615 |
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| SubjectTerms | aldehydes amination heterogeneous catalysis hydrogenation ketones nitriles |
| Title | The Reductive Amination of Aldehydes and Ketones and the Hydrogenation of Nitriles: Mechanistic Aspects and Selectivity Control |
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