Inhibition of Enone Reduction in Aqueous-Phase Pauson-Khand Reactions

Marie E. Krafft; James A. Wright; Llorente V. R. Boñaga

doi:10.1055/s-2004-836053

LETTER

Inhibition of Enone Reduction in Aqueous-Phase Pauson-Khand Reactions

Marie E. Krafft*, James A. Wright, Llorente V. R. Boñaga
Department of Chemistry and Biochemistry, The Florida State University, Tallahassee, FL, 32306-4390, USA
Fax: +1(850)6447409; e-Mail: mek@chem.fsu.edu;

Abstract

All articles of this category

Abstract

NMO-promoted room temperature cyclizations of the cobalt carbonyl complexes of substrates bearing terminal and internal alkynes gave exclusively the Pauson-Khand (PK) reaction adducts in a water-Triton X^®-100 medium.

Key words

alkynes - aqueous-phase - cycloadditions - green chemistry - Pauson-Khand reaction

Full Text

References

For reactions in aqueous media, see:

1a Lindström UM. Chem. Rev. 2002, 102: 2751

1b Aqueous-Phase Organometallic Catalysis Cornils B. Herrmann WA. Wiley-VCH; Weinheim: 1998.

1c Li CJ. Chan TH. Organic Reactions in Aqueous Media John Wiley and Sons; New York: 1997.

1d Horvath IT. Joo F. Aqueous Organometallic Chemistry and Catalysis Kluwer Academic; Dordrecht, The Netherlands: 1995.

1e For reactions in ionic liquids, see: Song CE. Chem. Commun. 2004, 1033

1f Sheldon R. Chem. Commun. 2001, 2399

1g For PK reaction in supercritical fluids, see: Jeong N. Wang SH. Lee YW. Lim JS. J. Am. Chem. Soc. 1997, 119: 10549

For recent reviews, see:

2a Blanco-Urgoiti J. Añorbe L. Perez-Serrano L. Dominguez G. Perez-Castells J. Chem. Soc. Rev. 2004, 33: 32

2b Gibson SE. Stevenazzi A. Angew. Chem. Int. Ed. 2003, 42: 1800 ; and references therein

For PK reactions in water, see:

3a Boñaga LVR. Wright JA. Krafft ME. Chem. Commun. 2004, 1746

3b Krafft ME. Wright JA. Boñaga LVR. Tetrahedron Lett. 2003, 44: 3417

3c Son SU. Lee SI. Chung YK. Kim SW. Hyeon T. Org. Lett. 2002, 4: 277

3d For PK reactions in ionic liquids, see: Becheanu A. Laschat S. Synlett 2002, 1865

3e For PK-type reactions in water, see: Koji F. Morimoto T. Tsutsumi K. Kakiuchi K. Angew. Chem. Int. Ed. 2003, 42: 2409

3f Su WH. Choi M. Lee SI. Chung YK. Synthesis 2003, 2169

4a Krafft ME. Boñaga LVR. Wright JA. Hirosawa C. J. Org. Chem. 2002, 67: 1233 ; and references therein

4b See also: Son SU. Park KH. Chung YK. Org. Lett. 2002, 4: 3983 ; this reference uses THF instead of water as the solvent for the reductive PKR

5 Shambayati S. Crowe WE. Schreiber SL. Tetrahedron Lett. 1990, 31: 5289

6 Jeong N. Chung YK. Lee BY. Lee SH. Yoo S.-E. Synlett 1991, 204

7 Krafft ME. Boñaga LVR. Hirosawa C. J. Org. Chem. 2001, 66: 3004 ; and references therein

For a review of side reactions observed under the PK reaction conditions, see:

8a Boñaga LVR. Krafft ME. Tetrahedron 2004, 60: 9795

8b For specific examples, see also: Lee H.-Y. An M. Sohn J.-H. Bull. Korean Chem. Soc. 2003, 24: 539

8c Cassayre J. Zard AZ. J. Organomet. Chem. 2001, 64: 316

8d Pérez-Serrano L. Blanco-Urgoiti J. Casarrubios L. Dominguez G. Pérez-Castells J. J. Org. Chem. 2000, 65: 3513

8e Sugihara T. Yamada M. Yamaguchi M. Nishizawa M. Synlett 1999, 771