Propargylation of aromatic compounds with propargylic alcohols catalyzed by a cationic diruthenium complex

Angewandte Chemie - International Edition

Volumn 42, Issue 13, 2003, Pages 1495-1498

  Nishibayashi, Yoshiaki ^a   Inada, Youichi ^a   Yoshikawa, Masato ^a   Hidai, Masanobu ^b   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Alkynes; Aromatic substitution; C H activation; Ruthenium; S ligands

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; ENVIRONMENTAL IMPACT; SYNTHESIS (CHEMICAL);

PROPARGYLATION;

ALCOHOLS;

ALCOHOL DERIVATIVE; AROMATIC COMPOUND; CATION; RUTHENIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; GAS LIQUID CHROMATOGRAPHY; PROPARGYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE;

EID: 0037418980     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250532     Document Type: Article

References (24)

1. Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. Hidai, S. Uemura, J. Am. Chem. Soc. 2002, 124, 11846.
2. The thiolate-bridged diruthenium complexes have been found to provide unique bimetallic reaction sites for activation and transformation of various terminal alkynes, see: Y. Nishibayashi, M. Yamanashi, I. Wakiji, M. Hidai, Angew. Chem. 2000, 112, 3031; Angew. Chem. Int. Ed. 2000, 39, 2909, and references therein.
3. The thiolate-bridged diruthenium complexes have been found to provide unique bimetallic reaction sites for activation and transformation of various terminal alkynes, see: Y. Nishibayashi, M. Yamanashi, I. Wakiji, M. Hidai, Angew. Chem. 2000, 112, 3031; Angew. Chem. Int. Ed. 2000, 39, 2909, and references therein.
4. a) Y. Nishibayashi, I. Wakiji, M. Hidai, J. Am. Chem. Soc. 2000, 122, 11019;
5. b) Y. Nishibayashi, I. Wakiji, Y. Ishii, S. Uemura, M. Hidai, J. Am. Chem. Soc. 2001, 123, 3393;
6. c) Y. Nishibayashi, Y. Inada, M. Hidai, S. Uemura, J. Am. Chem. Soc. 2002, 124, 7900;
7. d) Y. Inada, Y. Nishibayashi, M. Hidai, S. Uemura, J. Am. Chem. Soc. 2002, 124, 15172.
8. K. Tanaka, H. Aoki, H. Hosomi, S. Ohba, Org. Lett. 2000, 2, 2133.
9. For recent reviews, see a) C.-T. Chen, Coord. Chem. Rev. 1999, 190-192, 1143;
10. b) A. Wojcicki, Inorg. Chem. Commun. 2002, 5, 82.
11. For recent examples, see a) S. Ogoshi, T. Nishida, Y. Fukunishi, K. Tatsumi, H. Kurosawa, J. Organomet. Chem. 2001, 620, 190;
12. b) C. P. Casey, T. M. Boller, S. Kraft, I. A. Guzei, J. Am. Chem. Soc. 2002, 124, 13215.
13. G. A. Olah, Friedel-Crafts and Related Reactions, Interscience, New York, 1964.
14. a) T. Ishikawa, M. Okano, T. Aikawa, S. Saito, J. Org. Chem. 2001, 66, 4635;
15. b) T. J. J. Müller, Eur. J. Org. Chem. 2001, 2021, and references therein.
16. For recent reviews, see a) K. M. Nicholas, Acc. Chem. Res. 1987, 20, 207;
17. b) A. J. M. Caffyn, K. M. Nicholas in Comprehensive Organometallic Chemistry II, Vol. 12 (Eds.: E. W. Abel, G. A. Stone, G. Wilkinson,) Pergamon, New York, 1995, chap. 7.1;
18. c) J. R. Green, Curr. Org. Chem. 2001, 5, 811;
19. d) B. J. Teobald, Tetrahedron 2002, 58, 4133.
20. For recent examples, see a) K.-D. Roth, Synlett 1993, 529;
21. b) A. V. Muehldorf, A. Guzman-Perez, A. F. Klug, Tetrahedron Lett. 1994, 35, 8755;
22. c) D. D. Grove, J. R. Corte, R. P. Spencer, M. E. Pauly, N. P. Rath, J. Chem. Soc. Chem. Commun. 1994, 49;
23. d) J.-Y. LeBrazidec, P. J. Kocienski, J. D. Connolly, K. W. Muir, J. Chem. Soc. Perkin Trans. 1 1998, 2475;
24. e) R. Guo, J. R. Green, Chem. Commun. 1999, 2503.