Coupling of alkynes on a Pd-Pd bond to generate an electrophilic μ- butenediylidene moiety

Angewandte Chemie - International Edition

Volumn 39, Issue 3, 2000, Pages 537-540

  Murahashi, Tetsuro ^a   Otani, Toshiaki ^a   Okuno, Taketoshi ^a   Kurosawa, Hideo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Alkynes; C C coupling; Palladium

Indexed keywords

ALKYNE; LIGAND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CRYSTAL STRUCTURE; DIMERIZATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; X RAY DIFFRACTION;

EID: 0034603146     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000204)39:3<537::AID-ANIE537>3.0.CO;2-S     Document Type: Article

References (41)

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12. 2], which has a different formal valency of the metal centers from 3, has also been structurally characterized; f) R. Diercks, L. Stamp, J. Kopf, H. tom Dieck, Angew. Chem. 1984, 96, 891; Angew. Chem. Int. Ed. Engl. 1984, 23, 893.
13. 2], which has a different formal valency of the metal centers from 3, has also been structurally characterized; f) R. Diercks, L. Stamp, J. Kopf, H. tom Dieck, Angew. Chem. 1984, 96, 891; Angew. Chem. Int. Ed. Engl. 1984, 23, 893.
14. 2], which has a different formal valency of the metal centers from 3, has also been structurally characterized; f) R. Diercks, L. Stamp, J. Kopf, H. tom Dieck, Angew. Chem. 1984, 96, 891; Angew. Chem. Int. Ed. Engl. 1984, 23, 893.
15. 2], which has a different formal valency of the metal centers from 3, has also been structurally characterized; f) R. Diercks, L. Stamp, J. Kopf, H. tom Dieck, Angew. Chem. 1984, 96, 891; Angew. Chem. Int. Ed. Engl. 1984, 23, 893.
16. 2], which has a different formal valency of the metal centers from 3, has also been structurally characterized; f) R. Diercks, L. Stamp, J. Kopf, H. tom Dieck, Angew. Chem. 1984, 96, 891; Angew. Chem. Int. Ed. Engl. 1984, 23, 893.
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23. Metallacyclopentenyl complexes derived from acetylenes are very rare: H. Yamazaki, K. Yasufuku, Y. Wakatsuki, Organometallics 1983, 2, 726.
24. 3 ligand with one of the three acetonitrile ligands of the major isomer; the two isomers interconvert rapidly at room temperature (see Experimental Section).
25. 1-benzene complexes have been reported: a) R. A. Bartlett, H. Chen, P. P. Power, Angew. Chem. 1989, 101, 325; Angew. Chem. Int. Ed. Engl. 1989, 28, 316; b) L. R. Falvello, J. Forniés, R. Navarro, V. Sicilia, M. Tomás, Angew. Chem. 1990, 102, 952; Angew. Chem. Int. Ed. Engl. 1990, 29, 891; c) L. R. Falvello, J. Forniés, R. Navarro, V. Sicilia, M. Tomás, J. Chem. Soc. Dalton Trans. 1994, 3143; d) P. Braunstein, U. Englert, G. E. Herberich, M. Neuschütz, Angew. Chem. 1995, 107, 1090; Angew. Chem. Int. Ed. Engl. 1995, 34, 1010.
26. 1-benzene complexes have been reported: a) R. A. Bartlett, H. Chen, P. P. Power, Angew. Chem. 1989, 101, 325; Angew. Chem. Int. Ed. Engl. 1989, 28, 316; b) L. R. Falvello, J. Forniés, R. Navarro, V. Sicilia, M. Tomás, Angew. Chem. 1990, 102, 952; Angew. Chem. Int. Ed. Engl. 1990, 29, 891; c) L. R. Falvello, J. Forniés, R. Navarro, V. Sicilia, M. Tomás, J. Chem. Soc. Dalton Trans. 1994, 3143; d) P. Braunstein, U. Englert, G. E. Herberich, M. Neuschütz, Angew. Chem. 1995, 107, 1090; Angew. Chem. Int. Ed. Engl. 1995, 34, 1010.
27. 1-benzene complexes have been reported: a) R. A. Bartlett, H. Chen, P. P. Power, Angew. Chem. 1989, 101, 325; Angew. Chem. Int. Ed. Engl. 1989, 28, 316; b) L. R. Falvello, J. Forniés, R. Navarro, V. Sicilia, M. Tomás, Angew. Chem. 1990, 102, 952; Angew. Chem. Int. Ed. Engl. 1990, 29, 891; c) L. R. Falvello, J. Forniés, R. Navarro, V. Sicilia, M. Tomás, J. Chem. Soc. Dalton Trans. 1994, 3143; d) P. Braunstein, U. Englert, G. E. Herberich, M. Neuschütz, Angew. Chem. 1995, 107, 1090; Angew. Chem. Int. Ed. Engl. 1995, 34, 1010.
28. 1-benzene complexes have been reported: a) R. A. Bartlett, H. Chen, P. P. Power, Angew. Chem. 1989, 101, 325; Angew. Chem. Int. Ed. Engl. 1989, 28, 316; b) L. R. Falvello, J. Forniés, R. Navarro, V. Sicilia, M. Tomás, Angew. Chem. 1990, 102, 952; Angew. Chem. Int. Ed. Engl. 1990, 29, 891; c) L. R. Falvello, J. Forniés, R. Navarro, V. Sicilia, M. Tomás, J. Chem. Soc. Dalton Trans. 1994, 3143; d) P. Braunstein, U. Englert, G. E. Herberich, M. Neuschütz, Angew. Chem. 1995, 107, 1090; Angew. Chem. Int. Ed. Engl. 1995, 34, 1010.
29. 1-benzene complexes have been reported: a) R. A. Bartlett, H. Chen, P. P. Power, Angew. Chem. 1989, 101, 325; Angew. Chem. Int. Ed. Engl. 1989, 28, 316; b) L. R. Falvello, J. Forniés, R. Navarro, V. Sicilia, M. Tomás, Angew. Chem. 1990, 102, 952; Angew. Chem. Int. Ed. Engl. 1990, 29, 891; c) L. R. Falvello, J. Forniés, R. Navarro, V. Sicilia, M. Tomás, J. Chem. Soc. Dalton Trans. 1994, 3143; d) P. Braunstein, U. Englert, G. E. Herberich, M. Neuschütz, Angew. Chem. 1995, 107, 1090; Angew. Chem. Int. Ed. Engl. 1995, 34, 1010.
30. 1-benzene complexes have been reported: a) R. A. Bartlett, H. Chen, P. P. Power, Angew. Chem. 1989, 101, 325; Angew. Chem. Int. Ed. Engl. 1989, 28, 316; b) L. R. Falvello, J. Forniés, R. Navarro, V. Sicilia, M. Tomás, Angew. Chem. 1990, 102, 952; Angew. Chem. Int. Ed. Engl. 1990, 29, 891; c) L. R. Falvello, J. Forniés, R. Navarro, V. Sicilia, M. Tomás, J. Chem. Soc. Dalton Trans. 1994, 3143; d) P. Braunstein, U. Englert, G. E. Herberich, M. Neuschütz, Angew. Chem. 1995, 107, 1090; Angew. Chem. Int. Ed. Engl. 1995, 34, 1010.
31. 1-benzene complexes have been reported: a) R. A. Bartlett, H. Chen, P. P. Power, Angew. Chem. 1989, 101, 325; Angew. Chem. Int. Ed. Engl. 1989, 28, 316; b) L. R. Falvello, J. Forniés, R. Navarro, V. Sicilia, M. Tomás, Angew. Chem. 1990, 102, 952; Angew. Chem. Int. Ed. Engl. 1990, 29, 891; c) L. R. Falvello, J. Forniés, R. Navarro, V. Sicilia, M. Tomás, J. Chem. Soc. Dalton Trans. 1994, 3143; d) P. Braunstein, U. Englert, G. E. Herberich, M. Neuschütz, Angew. Chem. 1995, 107, 1090; Angew. Chem. Int. Ed. Engl. 1995, 34, 1010.
32. 2+ (dppp = 1,3-bis(diphenylphosphanyl)propane) has a similar ipso-phenyl coordination structure: P. H. M. Budzelaar, P. W. N. M. van Leeuwen, C. F. Roobeek, A. G. Orpen, Organometallics 1992, 11, 23.
33. 1-coordinated phenyl ring maintained its aromaticity (C- C 1.361(7)-1.398(5) Å) and planarity, whereby P1 also lies on the same plane. The C1-P1-Pd1 angle of 118.5(1) is in the usual range for coordinated phosphane ligands.
34. 3 (x = 2,4,6) coordination was observed with other transition metals: b) G. B. Robertson, P. O. Whimp, J. Organomet. Chem. 1973, 60, C 11; c) R. Luck, R. H. Morris, J. F. Sawyer, Organometallics 1984, 3, 1009; d) H.-F. Hsu, S. R. Wilson, J. R. Shapley, Organometallics 1997, 16, 4937; e) I. Ara, L. R. Falvello, J. Forniés, E. Lalinde, A. Martín, F. Martínez, M. T. Moreno, Organometallics 1997, 16, 5392.
35. 3 (x = 2,4,6) coordination was observed with other transition metals: b) G. B. Robertson, P. O. Whimp, J. Organomet. Chem. 1973, 60, C 11; c) R. Luck, R. H. Morris, J. F. Sawyer, Organometallics 1984, 3, 1009; d) H.-F. Hsu, S. R. Wilson, J. R. Shapley, Organometallics 1997, 16, 4937; e) I. Ara, L. R. Falvello, J. Forniés, E. Lalinde, A. Martín, F. Martínez, M. T. Moreno, Organometallics 1997, 16, 5392.
36. 3 (x = 2,4,6) coordination was observed with other transition metals: b) G. B. Robertson, P. O. Whimp, J. Organomet. Chem. 1973, 60, C 11; c) R. Luck, R. H. Morris, J. F. Sawyer, Organometallics 1984, 3, 1009; d) H.-F. Hsu, S. R. Wilson, J. R. Shapley, Organometallics 1997, 16, 4937; e) I. Ara, L. R. Falvello, J. Forniés, E. Lalinde, A. Martín, F. Martínez, M. T. Moreno, Organometallics 1997, 16, 5392.
37. 3 (x = 2,4,6) coordination was observed with other transition metals: b) G. B. Robertson, P. O. Whimp, J. Organomet. Chem. 1973, 60, C 11; c) R. Luck, R. H. Morris, J. F. Sawyer, Organometallics 1984, 3, 1009; d) H.-F. Hsu, S. R. Wilson, J. R. Shapley, Organometallics 1997, 16, 4937; e) I. Ara, L. R. Falvello, J. Forniés, E. Lalinde, A. Martín, F. Martínez, M. T. Moreno, Organometallics 1997, 16, 5392.
38. 3 (x = 2,4,6) coordination was observed with other transition metals: b) G. B. Robertson, P. O. Whimp, J. Organomet. Chem. 1973, 60, C 11; c) R. Luck, R. H. Morris, J. F. Sawyer, Organometallics 1984, 3, 1009; d) H.-F. Hsu, S. R. Wilson, J. R. Shapley, Organometallics 1997, 16, 4937; e) I. Ara, L. R. Falvello, J. Forniés, E. Lalinde, A. Martín, F. Martínez, M. T. Moreno, Organometallics 1997, 16, 5392.
39. -[4] is much less labile than that of 5.
40. 2CPh and PhC≡CMe also reacted with 1 or 4, but more complicated results were obtained under the reaction conditions of Equation (1).
41. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-124471 (2). -124472 (3). and -124473 (4). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223-336-1133; e-mail: deposit@ccdc.cam.ac.uk).