Hydrovinylation and [2+2] cycloaddition reactions of alkynes and alkenes catalyzed by a well-defined cationic ruthenium-alkylidene complex

Organometallics

Volumn 18, Issue 11, 1999, Pages 2043-2045

  Yi, Chae S ^a   Lee, Do W ^a   Chen, Yuzhong ^a  

^a Marquette University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 3843116797     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990129l     Document Type: Article

References (40)

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16. 3 analogue of 1 have been extensively described in: Buil, M. L.; Elipe, S.; Esteruelas, M. A.; Oñate, E.; Peinado, E.; Ruiz, N. Organometallics 1997, 16, 5748, and references therein.
17. See the Supporting Information for the characterization data of these compounds.
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35. For example, the hydrovinylation reaction of PhC≡CPh in the presence of 5 or 6a yielded 43% of the hydrovinylation product 2a along with ca. 50% of the unreacted alkyne after 2 h under similar reaction conditions.
36. Protons α to the carbene carbon in electrophilic metal-carbene complexes are known to be mildly acidic. For representative examples, see: (a) Casey, C. P. In Transition Metal Organometallics in Organic Synthesis; Alper, H., Ed.; Academic Press: New York, 1976; Vol. 1. (b) Casey, C. P.; Vosejpka, P. C.; Askham, F. R. J. Am. Chem. Soc. 1990, 112, 3713. (c) Montgomery, J.; Wieber, G. M.; Hegedus, L. S. J. Am. Chem. Soc. 1990, 112, 6255.
37. Protons α to the carbene carbon in electrophilic metal-carbene complexes are known to be mildly acidic. For representative examples, see: (a) Casey, C. P. In Transition Metal Organometallics in Organic Synthesis; Alper, H., Ed.; Academic Press: New York, 1976; Vol. 1. (b) Casey, C. P.; Vosejpka, P. C.; Askham, F. R. J. Am. Chem. Soc. 1990, 112, 3713. (c) Montgomery, J.; Wieber, G. M.; Hegedus, L. S. J. Am. Chem. Soc. 1990, 112, 6255.
38. Protons α to the carbene carbon in electrophilic metal-carbene complexes are known to be mildly acidic. For representative examples, see: (a) Casey, C. P. In Transition Metal Organometallics in Organic Synthesis; Alper, H., Ed.; Academic Press: New York, 1976; Vol. 1. (b) Casey, C. P.; Vosejpka, P. C.; Askham, F. R. J. Am. Chem. Soc. 1990, 112, 3713. (c) Montgomery, J.; Wieber, G. M.; Hegedus, L. S. J. Am. Chem. Soc. 1990, 112, 6255.
39. 3 ligand.
40. 2 group from the secondary alkyl intermediate I, but the possibility of involving metallacyclopentene intermediate II still cannot be rigorously ruled out at the present time.