Carbon-carbon bond cleavage of diynes through the hydroamination with transition metal catalysts

Journal of the American Chemical Society

Volumn 125, Issue 22, 2003, Pages 6646-6647

  Shimada, Tomohiro ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CARBON; DIYNE DERIVATIVE; METAL; UNCLASSIFIED DRUG;

AMINATION; AMINOHYDROXYLATION; ANALYTIC METHOD; ARTICLE; CATALYSIS; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; METAL BINDING; MOLECULAR MODEL; REACTION ANALYSIS;

EID: 0038547891     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034105o     Document Type: Article

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23. Alkyne metathesis proceeds in a catalytic manner, but in our opinion, the metathesis is categorized as an exchange reaction of alkynes, and not as the C-C bond cleavage reaction mentioned in this paper. For review see: Bunz, U. H. F.; Kloppenburg, L. Angew. Chem., Int. Ed. 1999, 38, 478. See also: (a) Rosenthal, U.; Arndt, P.; Baumann, W.; Burlakov, V. V.; Spannenberg, A. J. Organomet. Chem. 2003, 670, 84. (b) Chisholm, M. H.; Davidson, E. R.; Quinlan, K. B. J. Am. Chem. Soc. 2002, 124, 15351.
24. Alkyne metathesis proceeds in a catalytic manner, but in our opinion, the metathesis is categorized as an exchange reaction of alkynes, and not as the C-C bond cleavage reaction mentioned in this paper. For review see: Bunz, U. H. F.; Kloppenburg, L. Angew. Chem., Int. Ed. 1999, 38, 478. See also: (a) Rosenthal, U.; Arndt, P.; Baumann, W.; Burlakov, V. V.; Spannenberg, A. J. Organomet. Chem. 2003, 670, 84. (b) Chisholm, M. H.; Davidson, E. R.; Quinlan, K. B. J. Am. Chem. Soc. 2002, 124, 15351.
25. Alkyne metathesis proceeds in a catalytic manner, but in our opinion, the metathesis is categorized as an exchange reaction of alkynes, and not as the C-C bond cleavage reaction mentioned in this paper. For review see: Bunz, U. H. F.; Kloppenburg, L. Angew. Chem., Int. Ed. 1999, 38, 478. See also: (a) Rosenthal, U.; Arndt, P.; Baumann, W.; Burlakov, V. V.; Spannenberg, A. J. Organomet. Chem. 2003, 670, 84. (b) Chisholm, M. H.; Davidson, E. R.; Quinlan, K. B. J. Am. Chem. Soc. 2002, 124, 15351.
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27. Shimada, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12670.
28. The Ru-catalyzed hydroamination of terminal alkynes, see: Tokunaga, M.; Eckert, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. 1999, 38, 3222.
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30. The precise reason for this electronic effect of the substituents is not clear, but a smilar effect was also observed in the Pd-catalyzed hydroamination of monoalkynes using o-aminophenols (unpublished results).
31. 2 (65%).
32. nBuOH was used instead of MeOH.
33. 1 takes an orthogonal direction to the oxazole plane.