Sequential ruthenium-catalyzed hydroamination and rhenium-catalyzed C-H bond activation leading to indene derivatives

Organic Letters

Volumn 8, Issue 13, 2006, Pages 2891-2893

  Kuninobu, Yoichiro ^a   Nishina, Yuta ^a   Takai, Kazuhiko ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

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Indexed keywords

EID: 33746141335     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0611292     Document Type: Article

References (20)

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13. 9 the procedure is applicable for terminal alkynes.
14. 1H NMR yields were determined by using 1,1,2,2-tetrachloroethane as an internal standard.
15. p-Anisidine gave indene derivative 3a in almost the same yield as aniline. However, cyclohexylamine did not provide 3a at all.
16. The electron-withdrawing group decreased the reactivity in both the ruthenium-catalyzed hydroamination and the rhenium-catalyzed formation of indene frameworks. This might be the main reason an indene derivative was not formed by using 1-ethynyl-4-trifluoromethylbenzene.
17. 2 (3.0 mol %) at 180 °C for 24 h gave 3a in 21% yield.
18. 6, and aniline gave indene derivatives.
19. (a) Kuninobu, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2005, 127, 13498.
20. (b) Kuninobu, Y.; Tokunaga, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2006, 128, 202.