Ruthenium-mediated regio- and stereoselective alkenylation of pyridine

Journal of the American Chemical Society

Volumn 125, Issue 16, 2003, Pages 4720-4721

  Murakami, Masahiro ^a   Hori, Seiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; COMPLEX FORMATION; CYCLOADDITION; ISOMER; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON TRANSPORT; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS; THERMODYNAMICS;

ALKENES; ALKYNES; CATALYSIS; ORGANOMETALLIC COMPOUNDS; PYRIDINES; RUTHENIUM; SILANES; STEREOISOMERISM;

EID: 0037462095     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029829z     Document Type: Article

References (27)

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9. Leading references for the ruthenium-catalyzed C-C bond-forming reactions: (a) Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599-2660. (b) Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311-323. (c) Puerta, M. C.; Valerga, P. Coord. Chem. Rev. 1999, 193-195, 977-1025. (d) Yi, C. S.; Liu, N. Synlett 1999, 281-287. (e) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067-2096. (f) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731-1769. (g) Rüba, E.; Mereiter, K.; Schmid, R.; Sapunov, V. N.; Kirchner, K.; Schottenberger, H.; Calhorda, M. J.; Veiros, L. F. Chem. Eur. J. 2002, 8, 3948-3961.
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13. A large excess of pyridine was needed for the success of the reaction. It probably favors displacement of PPh3 with the weaker ligand, pyridine.
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20. No isomerization was observed in the absence of the ruthenium catalyst.
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23. Protiodesilylation is often observed during the formation of vinylidene complexes: (a) Bruce, M. I.; Koutsantonis, G. A. Aust. J. Chem. 1991, 44, 207-217. (b) Bianchini, C.; Marchi, A.; Marvelli, L.; Peruzzini, M.; Romerosa, A.; Rossi, R. Organometallics. 1996, 15, 3804-3816. (c) Kawata, Y.; Sato, M. Organometallics 1997, 16, 1093-1096. This lability might be in conjunction with the relatively high acidity of HC=C=M.
24. Protiodesilylation is often observed during the formation of vinylidene complexes: (a) Bruce, M. I.; Koutsantonis, G. A. Aust. J. Chem. 1991, 44, 207-217. (b) Bianchini, C.; Marchi, A.; Marvelli, L.; Peruzzini, M.; Romerosa, A.; Rossi, R. Organometallics. 1996, 15, 3804-3816. (c) Kawata, Y.; Sato, M. Organometallics 1997, 16, 1093-1096. This lability might be in conjunction with the relatively high acidity of HC=C=M.
25. Protiodesilylation is often observed during the formation of vinylidene complexes: (a) Bruce, M. I.; Koutsantonis, G. A. Aust. J. Chem. 1991, 44, 207-217. (b) Bianchini, C.; Marchi, A.; Marvelli, L.; Peruzzini, M.; Romerosa, A.; Rossi, R. Organometallics. 1996, 15, 3804-3816. (c) Kawata, Y.; Sato, M. Organometallics 1997, 16, 1093-1096. This lability might be in conjunction with the relatively high acidity of HC=C=M.
26. 6 were used as the catalyst precursors.
27. Direct propargylation of aromatic compounds using a ruthenium complex has recently been reported: Nishibayashi, Y.; Yoshikawa, M.; Inada, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 11846-11847.