The first efficient hydroaminomethylation with ammonia: With dual metal catalysts and two-phase catalysis to primary amines

Angewandte Chemie - International Edition

Volumn 38, Issue 16, 1999, Pages 2372-2375

  Zimmermann, Burkhard ^c   Herwig, Jürgen ^a   Beller, Matthias ^b  

^a Celanese AG   (Germany)

^b UNIVERSITY OF ROSTOCK   (Germany)

^c TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Amines; Hydroaminomethylations; Hydroformylations; Hydrogenations; Two phase catalysis

Indexed keywords

ALIPHATIC AMINE; ALKENE; AMMONIA;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; HYDROGENATION; ISOMERISM; METHYLATION; NONHUMAN; REACTION ANALYSIS; SYNTHESIS;

EID: 0033549727     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990816)38:16<2372::AID-ANIE2372>3.0.CO;2-H     Document Type: Article

References (41)

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2. Reviews on hydroamination: a) T. Müller, M. Beller, Chem. Rev. 1998, 98, 675; b) J.-J. Brunet, D. Neubecker, F. Niedercorn, J. Mol. Catal. 1989, 49, 253; c) D. M. Roundhill, Chem. Rev. 1992, 92, 1; d) D. Steinborn, R. Taube, Z. Chem. 1986, 26, 349.
3. Reviews on hydroamination: a) T. Müller, M. Beller, Chem. Rev. 1998, 98, 675; b) J.-J. Brunet, D. Neubecker, F. Niedercorn, J. Mol. Catal. 1989, 49, 253; c) D. M. Roundhill, Chem. Rev. 1992, 92, 1; d) D. Steinborn, R. Taube, Z. Chem. 1986, 26, 349.
4. Reviews on hydroamination: a) T. Müller, M. Beller, Chem. Rev. 1998, 98, 675; b) J.-J. Brunet, D. Neubecker, F. Niedercorn, J. Mol. Catal. 1989, 49, 253; c) D. M. Roundhill, Chem. Rev. 1992, 92, 1; d) D. Steinborn, R. Taube, Z. Chem. 1986, 26, 349.
5. Reviews on hydroamination: a) T. Müller, M. Beller, Chem. Rev. 1998, 98, 675; b) J.-J. Brunet, D. Neubecker, F. Niedercorn, J. Mol. Catal. 1989, 49, 253; c) D. M. Roundhill, Chem. Rev. 1992, 92, 1; d) D. Steinborn, R. Taube, Z. Chem. 1986, 26, 349.
6. Hydroaminomethylation: a) W. Reppe, H. Vetter, Liebigs Ann. Chem. 1953, 582, 133; b) A. F. M. Iqubal, Chim. Acta 1971, 45, 1440; c) R. M. Laine, J. Org. Chem. 1980, 45, 3370; d) K. Murata, A. Matsuda, T. Matsuda, J. Mol. Catal. 1984, 23, 121; e) F. Jachimowicz, J. W. Raksis, J. Org. Chem. 1982, 47, 44; f) E. MacEntire, J. F. Knifton (Texaco Inc.), EP-B 240193, 1987 [Chem. Abstr. 1989, 110, 134785h]; g) J. J. Brunet, D. Neibecker, F. Agbossou, R. S. Srivastava, J. Mol. Catal. 1994, 87. 233; h) E. Drent, A. J. M. Breed (Shell Int. Res. M.), EP-B 457386. 1992 [Chem. Abstr. 1992, 116, 83212h]; i) S. Törös, I. Gemes-Pesci, B. Heil, S. Maho, Z. Tuber, J. Chem. Soc. Chem. Commun. 1992, 585; j) T. Baig, P. Kalck, J. Chem. Soc. Chem. Commun. 1992, 1373; k) T. Baig, J. Molinier, P. Kalck, J. Organomet. Chem. 1993, 455, 219; l) M. D. Jones, J. Organomet. Chem. 1989, 366, 403; m) G. Diekhaus, D. Kampmann, C. Kniep, T. Müller, J. Walter, J. Weber (Hoechst AG), DE-B 4334809, 1993 [Chem. Abstr. 1995, 122, 314160g]; n) H. Schaffrath, W. Keim, J. Mol. Catal. 1999, 140, 107.
7. Hydroaminomethylation: a) W. Reppe, H. Vetter, Liebigs Ann. Chem. 1953, 582, 133; b) A. F. M. Iqubal, Chim. Acta 1971, 45, 1440; c) R. M. Laine, J. Org. Chem. 1980, 45, 3370; d) K. Murata, A. Matsuda, T. Matsuda, J. Mol. Catal. 1984, 23, 121; e) F. Jachimowicz, J. W. Raksis, J. Org. Chem. 1982, 47, 44; f) E. MacEntire, J. F. Knifton (Texaco Inc.), EP-B 240193, 1987 [Chem. Abstr. 1989, 110, 134785h]; g) J. J. Brunet, D. Neibecker, F. Agbossou, R. S. Srivastava, J. Mol. Catal. 1994, 87. 233; h) E. Drent, A. J. M. Breed (Shell Int. Res. M.), EP-B 457386. 1992 [Chem. Abstr. 1992, 116, 83212h]; i) S. Törös, I. Gemes-Pesci, B. Heil, S. Maho, Z. Tuber, J. Chem. Soc. Chem. Commun. 1992, 585; j) T. Baig, P. Kalck, J. Chem. Soc. Chem. Commun. 1992, 1373; k) T. Baig, J. Molinier, P. Kalck, J. Organomet. Chem. 1993, 455, 219; l) M. D. Jones, J. Organomet. Chem. 1989, 366, 403; m) G. Diekhaus, D. Kampmann, C. Kniep, T. Müller, J. Walter, J. Weber (Hoechst AG), DE-B 4334809, 1993 [Chem. Abstr. 1995, 122, 314160g]; n) H. Schaffrath, W. Keim, J. Mol. Catal. 1999, 140, 107.
8. Hydroaminomethylation: a) W. Reppe, H. Vetter, Liebigs Ann. Chem. 1953, 582, 133; b) A. F. M. Iqubal, Chim. Acta 1971, 45, 1440; c) R. M. Laine, J. Org. Chem. 1980, 45, 3370; d) K. Murata, A. Matsuda, T. Matsuda, J. Mol. Catal. 1984, 23, 121; e) F. Jachimowicz, J. W. Raksis, J. Org. Chem. 1982, 47, 44; f) E. MacEntire, J. F. Knifton (Texaco Inc.), EP-B 240193, 1987 [Chem. Abstr. 1989, 110, 134785h]; g) J. J. Brunet, D. Neibecker, F. Agbossou, R. S. Srivastava, J. Mol. Catal. 1994, 87. 233; h) E. Drent, A. J. M. Breed (Shell Int. Res. M.), EP-B 457386. 1992 [Chem. Abstr. 1992, 116, 83212h]; i) S. Törös, I. Gemes-Pesci, B. Heil, S. Maho, Z. Tuber, J. Chem. Soc. Chem. Commun. 1992, 585; j) T. Baig, P. Kalck, J. Chem. Soc. Chem. Commun. 1992, 1373; k) T. Baig, J. Molinier, P. Kalck, J. Organomet. Chem. 1993, 455, 219; l) M. D. Jones, J. Organomet. Chem. 1989, 366, 403; m) G. Diekhaus, D. Kampmann, C. Kniep, T. Müller, J. Walter, J. Weber (Hoechst AG), DE-B 4334809, 1993 [Chem. Abstr. 1995, 122, 314160g]; n) H. Schaffrath, W. Keim, J. Mol. Catal. 1999, 140, 107.
9. Hydroaminomethylation: a) W. Reppe, H. Vetter, Liebigs Ann. Chem. 1953, 582, 133; b) A. F. M. Iqubal, Chim. Acta 1971, 45, 1440; c) R. M. Laine, J. Org. Chem. 1980, 45, 3370; d) K. Murata, A. Matsuda, T. Matsuda, J. Mol. Catal. 1984, 23, 121; e) F. Jachimowicz, J. W. Raksis, J. Org. Chem. 1982, 47, 44; f) E. MacEntire, J. F. Knifton (Texaco Inc.), EP-B 240193, 1987 [Chem. Abstr. 1989, 110, 134785h]; g) J. J. Brunet, D. Neibecker, F. Agbossou, R. S. Srivastava, J. Mol. Catal. 1994, 87. 233; h) E. Drent, A. J. M. Breed (Shell Int. Res. M.), EP-B 457386. 1992 [Chem. Abstr. 1992, 116, 83212h]; i) S. Törös, I. Gemes-Pesci, B. Heil, S. Maho, Z. Tuber, J. Chem. Soc. Chem. Commun. 1992, 585; j) T. Baig, P. Kalck, J. Chem. Soc. Chem. Commun. 1992, 1373; k) T. Baig, J. Molinier, P. Kalck, J. Organomet. Chem. 1993, 455, 219; l) M. D. Jones, J. Organomet. Chem. 1989, 366, 403; m) G. Diekhaus, D. Kampmann, C. Kniep, T. Müller, J. Walter, J. Weber (Hoechst AG), DE-B 4334809, 1993 [Chem. Abstr. 1995, 122, 314160g]; n) H. Schaffrath, W. Keim, J. Mol. Catal. 1999, 140, 107.
10. Hydroaminomethylation: a) W. Reppe, H. Vetter, Liebigs Ann. Chem. 1953, 582, 133; b) A. F. M. Iqubal, Chim. Acta 1971, 45, 1440; c) R. M. Laine, J. Org. Chem. 1980, 45, 3370; d) K. Murata, A. Matsuda, T. Matsuda, J. Mol. Catal. 1984, 23, 121; e) F. Jachimowicz, J. W. Raksis, J. Org. Chem. 1982, 47, 44; f) E. MacEntire, J. F. Knifton (Texaco Inc.), EP-B 240193, 1987 [Chem. Abstr. 1989, 110, 134785h]; g) J. J. Brunet, D. Neibecker, F. Agbossou, R. S. Srivastava, J. Mol. Catal. 1994, 87. 233; h) E. Drent, A. J. M. Breed (Shell Int. Res. M.), EP-B 457386. 1992 [Chem. Abstr. 1992, 116, 83212h]; i) S. Törös, I. Gemes-Pesci, B. Heil, S. Maho, Z. Tuber, J. Chem. Soc. Chem. Commun. 1992, 585; j) T. Baig, P. Kalck, J. Chem. Soc. Chem. Commun. 1992, 1373; k) T. Baig, J. Molinier, P. Kalck, J. Organomet. Chem. 1993, 455, 219; l) M. D. Jones, J. Organomet. Chem. 1989, 366, 403; m) G. Diekhaus, D. Kampmann, C. Kniep, T. Müller, J. Walter, J. Weber (Hoechst AG), DE-B 4334809, 1993 [Chem. Abstr. 1995, 122, 314160g]; n) H. Schaffrath, W. Keim, J. Mol. Catal. 1999, 140, 107.
11. Hydroaminomethylation: a) W. Reppe, H. Vetter, Liebigs Ann. Chem. 1953, 582, 133; b) A. F. M. Iqubal, Chim. Acta 1971, 45, 1440; c) R. M. Laine, J. Org. Chem. 1980, 45, 3370; d) K. Murata, A. Matsuda, T. Matsuda, J. Mol. Catal. 1984, 23, 121; e) F. Jachimowicz, J. W. Raksis, J. Org. Chem. 1982, 47, 44; f) E. MacEntire, J. F. Knifton (Texaco Inc.), EP-B 240193, 1987 [Chem. Abstr. 1989, 110, 134785h]; g) J. J. Brunet, D. Neibecker, F. Agbossou, R. S. Srivastava, J. Mol. Catal. 1994, 87. 233; h) E. Drent, A. J. M. Breed (Shell Int. Res. M.), EP-B 457386. 1992 [Chem. Abstr. 1992, 116, 83212h]; i) S. Törös, I. Gemes-Pesci, B. Heil, S. Maho, Z. Tuber, J. Chem. Soc. Chem. Commun. 1992, 585; j) T. Baig, P. Kalck, J. Chem. Soc. Chem. Commun. 1992, 1373; k) T. Baig, J. Molinier, P. Kalck, J. Organomet. Chem. 1993, 455, 219; l) M. D. Jones, J. Organomet. Chem. 1989, 366, 403; m) G. Diekhaus, D. Kampmann, C. Kniep, T. Müller, J. Walter, J. Weber (Hoechst AG), DE-B 4334809, 1993 [Chem. Abstr. 1995, 122, 314160g]; n) H. Schaffrath, W. Keim, J. Mol. Catal. 1999, 140, 107.
12. Hydroaminomethylation: a) W. Reppe, H. Vetter, Liebigs Ann. Chem. 1953, 582, 133; b) A. F. M. Iqubal, Chim. Acta 1971, 45, 1440; c) R. M. Laine, J. Org. Chem. 1980, 45, 3370; d) K. Murata, A. Matsuda, T. Matsuda, J. Mol. Catal. 1984, 23, 121; e) F. Jachimowicz, J. W. Raksis, J. Org. Chem. 1982, 47, 44; f) E. MacEntire, J. F. Knifton (Texaco Inc.), EP-B 240193, 1987 [Chem. Abstr. 1989, 110, 134785h]; g) J. J. Brunet, D. Neibecker, F. Agbossou, R. S. Srivastava, J. Mol. Catal. 1994, 87. 233; h) E. Drent, A. J. M. Breed (Shell Int. Res. M.), EP-B 457386. 1992 [Chem. Abstr. 1992, 116, 83212h]; i) S. Törös, I. Gemes-Pesci, B. Heil, S. Maho, Z. Tuber, J. Chem. Soc. Chem. Commun. 1992, 585; j) T. Baig, P. Kalck, J. Chem. Soc. Chem. Commun. 1992, 1373; k) T. Baig, J. Molinier, P. Kalck, J. Organomet. Chem. 1993, 455, 219; l) M. D. Jones, J. Organomet. Chem. 1989, 366, 403; m) G. Diekhaus, D. Kampmann, C. Kniep, T. Müller, J. Walter, J. Weber (Hoechst AG), DE-B 4334809, 1993 [Chem. Abstr. 1995, 122, 314160g]; n) H. Schaffrath, W. Keim, J. Mol. Catal. 1999, 140, 107.
13. Hydroaminomethylation: a) W. Reppe, H. Vetter, Liebigs Ann. Chem. 1953, 582, 133; b) A. F. M. Iqubal, Chim. Acta 1971, 45, 1440; c) R. M. Laine, J. Org. Chem. 1980, 45, 3370; d) K. Murata, A. Matsuda, T. Matsuda, J. Mol. Catal. 1984, 23, 121; e) F. Jachimowicz, J. W. Raksis, J. Org. Chem. 1982, 47, 44; f) E. MacEntire, J. F. Knifton (Texaco Inc.), EP-B 240193, 1987 [Chem. Abstr. 1989, 110, 134785h]; g) J. J. Brunet, D. Neibecker, F. Agbossou, R. S. Srivastava, J. Mol. Catal. 1994, 87. 233; h) E. Drent, A. J. M. Breed (Shell Int. Res. M.), EP-B 457386. 1992 [Chem. Abstr. 1992, 116, 83212h]; i) S. Törös, I. Gemes-Pesci, B. Heil, S. Maho, Z. Tuber, J. Chem. Soc. Chem. Commun. 1992, 585; j) T. Baig, P. Kalck, J. Chem. Soc. Chem. Commun. 1992, 1373; k) T. Baig, J. Molinier, P. Kalck, J. Organomet. Chem. 1993, 455, 219; l) M. D. Jones, J. Organomet. Chem. 1989, 366, 403; m) G. Diekhaus, D. Kampmann, C. Kniep, T. Müller, J. Walter, J. Weber (Hoechst AG), DE-B 4334809, 1993 [Chem. Abstr. 1995, 122, 314160g]; n) H. Schaffrath, W. Keim, J. Mol. Catal. 1999, 140, 107.
14. Hydroaminomethylation: a) W. Reppe, H. Vetter, Liebigs Ann. Chem. 1953, 582, 133; b) A. F. M. Iqubal, Chim. Acta 1971, 45, 1440; c) R. M. Laine, J. Org. Chem. 1980, 45, 3370; d) K. Murata, A. Matsuda, T. Matsuda, J. Mol. Catal. 1984, 23, 121; e) F. Jachimowicz, J. W. Raksis, J. Org. Chem. 1982, 47, 44; f) E. MacEntire, J. F. Knifton (Texaco Inc.), EP-B 240193, 1987 [Chem. Abstr. 1989, 110, 134785h]; g) J. J. Brunet, D. Neibecker, F. Agbossou, R. S. Srivastava, J. Mol. Catal. 1994, 87. 233; h) E. Drent, A. J. M. Breed (Shell Int. Res. M.), EP-B 457386. 1992 [Chem. Abstr. 1992, 116, 83212h]; i) S. Törös, I. Gemes-Pesci, B. Heil, S. Maho, Z. Tuber, J. Chem. Soc. Chem. Commun. 1992, 585; j) T. Baig, P. Kalck, J. Chem. Soc. Chem. Commun. 1992, 1373; k) T. Baig, J. Molinier, P. Kalck, J. Organomet. Chem. 1993, 455, 219; l) M. D. Jones, J. Organomet. Chem. 1989, 366, 403; m) G. Diekhaus, D. Kampmann, C. Kniep, T. Müller, J. Walter, J. Weber (Hoechst AG), DE-B 4334809, 1993 [Chem. Abstr. 1995, 122, 314160g]; n) H. Schaffrath, W. Keim, J. Mol. Catal. 1999, 140, 107.
15. Hydroaminomethylation: a) W. Reppe, H. Vetter, Liebigs Ann. Chem. 1953, 582, 133; b) A. F. M. Iqubal, Chim. Acta 1971, 45, 1440; c) R. M. Laine, J. Org. Chem. 1980, 45, 3370; d) K. Murata, A. Matsuda, T. Matsuda, J. Mol. Catal. 1984, 23, 121; e) F. Jachimowicz, J. W. Raksis, J. Org. Chem. 1982, 47, 44; f) E. MacEntire, J. F. Knifton (Texaco Inc.), EP-B 240193, 1987 [Chem. Abstr. 1989, 110, 134785h]; g) J. J. Brunet, D. Neibecker, F. Agbossou, R. S. Srivastava, J. Mol. Catal. 1994, 87. 233; h) E. Drent, A. J. M. Breed (Shell Int. Res. M.), EP-B 457386. 1992 [Chem. Abstr. 1992, 116, 83212h]; i) S. Törös, I. Gemes-Pesci, B. Heil, S. Maho, Z. Tuber, J. Chem. Soc. Chem. Commun. 1992, 585; j) T. Baig, P. Kalck, J. Chem. Soc. Chem. Commun. 1992, 1373; k) T. Baig, J. Molinier, P. Kalck, J. Organomet. Chem. 1993, 455, 219; l) M. D. Jones, J. Organomet. Chem. 1989, 366, 403; m) G. Diekhaus, D. Kampmann, C. Kniep, T. Müller, J. Walter, J. Weber (Hoechst AG), DE-B 4334809, 1993 [Chem. Abstr. 1995, 122, 314160g]; n) H. Schaffrath, W. Keim, J. Mol. Catal. 1999, 140, 107.
16. Hydroaminomethylation: a) W. Reppe, H. Vetter, Liebigs Ann. Chem. 1953, 582, 133; b) A. F. M. Iqubal, Chim. Acta 1971, 45, 1440; c) R. M. Laine, J. Org. Chem. 1980, 45, 3370; d) K. Murata, A. Matsuda, T. Matsuda, J. Mol. Catal. 1984, 23, 121; e) F. Jachimowicz, J. W. Raksis, J. Org. Chem. 1982, 47, 44; f) E. MacEntire, J. F. Knifton (Texaco Inc.), EP-B 240193, 1987 [Chem. Abstr. 1989, 110, 134785h]; g) J. J. Brunet, D. Neibecker, F. Agbossou, R. S. Srivastava, J. Mol. Catal. 1994, 87. 233; h) E. Drent, A. J. M. Breed (Shell Int. Res. M.), EP-B 457386. 1992 [Chem. Abstr. 1992, 116, 83212h]; i) S. Törös, I. Gemes-Pesci, B. Heil, S. Maho, Z. Tuber, J. Chem. Soc. Chem. Commun. 1992, 585; j) T. Baig, P. Kalck, J. Chem. Soc. Chem. Commun. 1992, 1373; k) T. Baig, J. Molinier, P. Kalck, J. Organomet. Chem. 1993, 455, 219; l) M. D. Jones, J. Organomet. Chem. 1989, 366, 403; m) G. Diekhaus, D. Kampmann, C. Kniep, T. Müller, J. Walter, J. Weber (Hoechst AG), DE-B 4334809, 1993 [Chem. Abstr. 1995, 122, 314160g]; n) H. Schaffrath, W. Keim, J. Mol. Catal. 1999, 140, 107.
17. Hydroaminomethylation: a) W. Reppe, H. Vetter, Liebigs Ann. Chem. 1953, 582, 133; b) A. F. M. Iqubal, Chim. Acta 1971, 45, 1440; c) R. M. Laine, J. Org. Chem. 1980, 45, 3370; d) K. Murata, A. Matsuda, T. Matsuda, J. Mol. Catal. 1984, 23, 121; e) F. Jachimowicz, J. W. Raksis, J. Org. Chem. 1982, 47, 44; f) E. MacEntire, J. F. Knifton (Texaco Inc.), EP-B 240193, 1987 [Chem. Abstr. 1989, 110, 134785h]; g) J. J. Brunet, D. Neibecker, F. Agbossou, R. S. Srivastava, J. Mol. Catal. 1994, 87. 233; h) E. Drent, A. J. M. Breed (Shell Int. Res. M.), EP-B 457386. 1992 [Chem. Abstr. 1992, 116, 83212h]; i) S. Törös, I. Gemes-Pesci, B. Heil, S. Maho, Z. Tuber, J. Chem. Soc. Chem. Commun. 1992, 585; j) T. Baig, P. Kalck, J. Chem. Soc. Chem. Commun. 1992, 1373; k) T. Baig, J. Molinier, P. Kalck, J. Organomet. Chem. 1993, 455, 219; l) M. D. Jones, J. Organomet. Chem. 1989, 366, 403; m) G. Diekhaus, D. Kampmann, C. Kniep, T. Müller, J. Walter, J. Weber (Hoechst AG), DE-B 4334809, 1993 [Chem. Abstr. 1995, 122, 314160g]; n) H. Schaffrath, W. Keim, J. Mol. Catal. 1999, 140, 107.
18. Hydroaminomethylation: a) W. Reppe, H. Vetter, Liebigs Ann. Chem. 1953, 582, 133; b) A. F. M. Iqubal, Chim. Acta 1971, 45, 1440; c) R. M. Laine, J. Org. Chem. 1980, 45, 3370; d) K. Murata, A. Matsuda, T. Matsuda, J. Mol. Catal. 1984, 23, 121; e) F. Jachimowicz, J. W. Raksis, J. Org. Chem. 1982, 47, 44; f) E. MacEntire, J. F. Knifton (Texaco Inc.), EP-B 240193, 1987 [Chem. Abstr. 1989, 110, 134785h]; g) J. J. Brunet, D. Neibecker, F. Agbossou, R. S. Srivastava, J. Mol. Catal. 1994, 87. 233; h) E. Drent, A. J. M. Breed (Shell Int. Res. M.), EP-B 457386. 1992 [Chem. Abstr. 1992, 116, 83212h]; i) S. Törös, I. Gemes-Pesci, B. Heil, S. Maho, Z. Tuber, J. Chem. Soc. Chem. Commun. 1992, 585; j) T. Baig, P. Kalck, J. Chem. Soc. Chem. Commun. 1992, 1373; k) T. Baig, J. Molinier, P. Kalck, J. Organomet. Chem. 1993, 455, 219; l) M. D. Jones, J. Organomet. Chem. 1989, 366, 403; m) G. Diekhaus, D. Kampmann, C. Kniep, T. Müller, J. Walter, J. Weber (Hoechst AG), DE-B 4334809, 1993 [Chem. Abstr. 1995, 122, 314160g]; n) H. Schaffrath, W. Keim, J. Mol. Catal. 1999, 140, 107.
19. Hydroaminomethylation: a) W. Reppe, H. Vetter, Liebigs Ann. Chem. 1953, 582, 133; b) A. F. M. Iqubal, Chim. Acta 1971, 45, 1440; c) R. M. Laine, J. Org. Chem. 1980, 45, 3370; d) K. Murata, A. Matsuda, T. Matsuda, J. Mol. Catal. 1984, 23, 121; e) F. Jachimowicz, J. W. Raksis, J. Org. Chem. 1982, 47, 44; f) E. MacEntire, J. F. Knifton (Texaco Inc.), EP-B 240193, 1987 [Chem. Abstr. 1989, 110, 134785h]; g) J. J. Brunet, D. Neibecker, F. Agbossou, R. S. Srivastava, J. Mol. Catal. 1994, 87. 233; h) E. Drent, A. J. M. Breed (Shell Int. Res. M.), EP-B 457386. 1992 [Chem. Abstr. 1992, 116, 83212h]; i) S. Törös, I. Gemes-Pesci, B. Heil, S. Maho, Z. Tuber, J. Chem. Soc. Chem. Commun. 1992, 585; j) T. Baig, P. Kalck, J. Chem. Soc. Chem. Commun. 1992, 1373; k) T. Baig, J. Molinier, P. Kalck, J. Organomet. Chem. 1993, 455, 219; l) M. D. Jones, J. Organomet. Chem. 1989, 366, 403; m) G. Diekhaus, D. Kampmann, C. Kniep, T. Müller, J. Walter, J. Weber (Hoechst AG), DE-B 4334809, 1993 [Chem. Abstr. 1995, 122, 314160g]; n) H. Schaffrath, W. Keim, J. Mol. Catal. 1999, 140, 107.
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29. Recent reviews on two-phase catalysis: a) Aqueous-Phase Organometallic Catalysis. Concepts and Applications (Eds.: B. Cornils, W. A. Herrmann), WILEY-VCH, Weinheim, 1998; b) W. A. Herrmann, C. W. Kohlpaintner, Angew. Chem. 1993, 105, 1588; Angew. Chem. Int. Ed. Engl. 1993, 32, 1524; c) J. Mol. Catal. 1997, 116(1-2); d) P. Kalck, F. Monteil, Adv. Organomet. Chem. 1992, 34, 219.
30. Recent reviews on two-phase catalysis: a) Aqueous-Phase Organometallic Catalysis. Concepts and Applications (Eds.: B. Cornils, W. A. Herrmann), WILEY-VCH, Weinheim, 1998; b) W. A. Herrmann, C. W. Kohlpaintner, Angew. Chem. 1993, 105, 1588; Angew. Chem. Int. Ed. Engl. 1993, 32, 1524; c) J. Mol. Catal. 1997, 116(1-2); d) P. Kalck, F. Monteil, Adv. Organomet. Chem. 1992, 34, 219.
31. Recent reviews on two-phase catalysis: a) Aqueous-Phase Organometallic Catalysis. Concepts and Applications (Eds.: B. Cornils, W. A. Herrmann), WILEY-VCH, Weinheim, 1998; b) W. A. Herrmann, C. W. Kohlpaintner, Angew. Chem. 1993, 105, 1588; Angew. Chem. Int. Ed. Engl. 1993, 32, 1524; c) J. Mol. Catal. 1997, 116(1-2); d) P. Kalck, F. Monteil, Adv. Organomet. Chem. 1992, 34, 219.
32. Recent reviews on two-phase catalysis: a) Aqueous-Phase Organometallic Catalysis. Concepts and Applications (Eds.: B. Cornils, W. A. Herrmann), WILEY-VCH, Weinheim, 1998; b) W. A. Herrmann, C. W. Kohlpaintner, Angew. Chem. 1993, 105, 1588; Angew. Chem. Int. Ed. Engl. 1993, 32, 1524; c) J. Mol. Catal. 1997, 116(1-2); d) P. Kalck, F. Monteil, Adv. Organomet. Chem. 1992, 34, 219.
33. Recent reviews on two-phase catalysis: a) Aqueous-Phase Organometallic Catalysis. Concepts and Applications (Eds.: B. Cornils, W. A. Herrmann), WILEY-VCH, Weinheim, 1998; b) W. A. Herrmann, C. W. Kohlpaintner, Angew. Chem. 1993, 105, 1588; Angew. Chem. Int. Ed. Engl. 1993, 32, 1524; c) J. Mol. Catal. 1997, 116(1-2); d) P. Kalck, F. Monteil, Adv. Organomet. Chem. 1992, 34, 219.
34. a) Y. N. C. Chan, D. Meyer, J. A. Osborn, J. Chem. Soc. Chem. Commun. 1990, 869;
35. b) A. Benyei, F. Joo, J. Mol. Catal. 1990, 58, 151;
36. c) R. V. Chaudhari, B. M. Bhanage, S. S. Divekar, R. M. Deshpande (Council Sci. Ind. Res.), US-A 5650546, 1997 [Chem. Abstr. 1997, 127, 161588d];
37. d) F. Spindler, B. Pugin, H.-U. Blaser, Angew. Chem. 1990, 102, 561; Angew. Chem. Int. Ed. Engl. 1990, 29, 558.
38. d) F. Spindler, B. Pugin, H.-U. Blaser, Angew. Chem. 1990, 102, 561; Angew. Chem. Int. Ed. Engl. 1990, 29, 558.
39. The ligand BINAS was obtained from 1,1′-binaphthaline-2,2′-diylbis-(methylene)bis(diphenylphosphane) (NAPHOS) by direct sulfonation according to Herrmann et al. (W. A. Herrmann, G. P. Albanese, R. B. Manetsberger, P. Lappe, H. Bahrmann, Angew. Chem. 1995, 107, 893; Angew. Chem. Int. Ed. Engl. 1995, 34, 811).
40. The ligand BINAS was obtained from 1,1′-binaphthaline-2,2′-diylbis-(methylene)bis(diphenylphosphane) (NAPHOS) by direct sulfonation according to Herrmann et al. (W. A. Herrmann, G. P. Albanese, R. B. Manetsberger, P. Lappe, H. Bahrmann, Angew. Chem. 1995, 107, 893; Angew. Chem. Int. Ed. Engl. 1995, 34, 811).
41. 3:olefin = 0.5:1), respectively. An accurate determination of hydrogenation side reactions was not possible for technical reasons