Synlett 2003(9): 1295-1298
DOI: 10.1055/s-2003-40357
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium-Catalyzed [5+2] Cycloaddition Reactions in Water

Paul A. Wender*, Jennifer A. Love, Travis J. Williams
Department of Chemistry, Stanford University, Stanford, CA 94305, USA
Fax: +1(650)7250259; e-Mail: wenderp@leland.stanford.edu;
Further Information

Publication History

Received 17 December 2003
Publication Date:
30 June 2003 (online)

Abstract

A new water-soluble rhodium catalyst is reported along with its ability to effect [5+2] cycloaddition reactions in water. This water-soluble catalyst is recyclable, is readily separated from the organic product, and allows one to avoid or minimize the use of organic solvents, the major waste stream of most organic reactions.

    References

  • 1a Wender PA. Handy ST. Wright DL. Chem. Ind. (London)  1997,  765-769 
  • 1b Wender PA. Miller BL. Organic Synthesis: Theory and Applications   Vol. 2:  Hudlicky T. JAI Press; Greenwich: 1993.  p.27-66  
  • For general reviews, see
  • 2a Herrmann WA. Kohlpaintner CW. Angew. Chem., Int. Ed. Engl.  1993,  32:  1524-1544 ; Angew. Chem. 1993, 105, 1588-1608
  • 2b Verspui G. Brink G.-J. Sheldon R. Chemtracts  1999,  777-796 
  • 2c For recent, relevant examples of transition metal-mediated reactions in water, see: Uenishi J. Beau JM. Armstrong RW. Kishi Y. J. Am. Chem. Soc.  1987,  109:  4756-4758 
  • 2d See also: Okano T. Kaji M. Isotani S. Kiji J. Tetrahedron Lett.  1992,  33:  5547-5550 
  • 2e Genet JP. Blart E. Savignac M. Synlett  1992,  715-717 
  • 2f See further: Fremy G. Castanet Y. Grzybek R. Monflier E. Mortreux A. Trzeciak AM. Ziolkowski JJ. J. Organomet. Chem.  1995,  505:  11 -16
  • 2g Lynn DM. Mohr B. Grubbs RH. J. Am. Chem. Soc.  1998,  120:  1627-1628 
  • 2h Shirakawa S. Shimizu S. Sasaki Y. New J. Chem.  2001,  25:  777-779 
  • 2i For more examples see: Lautens M. Roy A. Fukuoka K. Fagnou K. Martin-Matute B. J. Am. Chem. Soc.  2001,  123:  5358-5359 
  • 2j Huang T. Meng Y. Venkatraman S. Wang O. Li C.-J. J. Am. Chem. Soc.  2001,  123:  7451-7452 
  • 3 Aqueous-phase Organometallic Catalysis: Concepts and Applications   Cornils B. Herrmann WA. Wiley; New York: 1998. 
  • 4a Wender PA. Jenkins TE. J. Am. Chem. Soc.  1989,  111:  6432-6434 
  • 4b Wender PA. Smith TE. J. Org. Chem.  1996,  61:  824-825 
  • 4c Wender PA. Smith TE. Tetrahedron  1998,  54:  1255-1275 
  • Intramolecular [5+2] reactions:
  • 5a Wender PA. Takahashi H. Witulski B. J. Am. Chem. Soc.  1995,  117:  4720-4721 
  • 5b Wender PA. Husfeld CO. Langkopf E. Love JA. J. Am. Chem. Soc.  1998,  120:  1940 -1941
  • 5c Wender PA. Husfeld CO. Langkopf E. Love JA. Pleuss N. Tetrahedron  1998,  54:  7203-7220 
  • 5d Wender PA. Sperandio D. J. Org. Chem.  1998,  63:  4164 -4165
  • 5e Wender PA. Glorius F. Husfeld CO. Langkopf E. Love JA. J. Am. Chem. Soc.  1999,  121:  5348-5349 
  • 5f Wender PA. Dyckman AJ. Husfeld CO. Kadereit D. Love JA. Rieck H. J. Am. Chem. Soc.  1999,  121:  10442-10443 
  • 5g Wender PA. Dyckman AJ. Org. Lett.  1999,  1:  2089-2092 
  • 5h Intermolecular [5+2] reactions: Wender PA. Rieck H. Fuji M. J. Am. Chem. Soc.  1998,  120:  10976-10977 
  • 5i See also: Wender PA. Dyckman AJ. Husfeld CO. Scanio MJC. Org. Lett.  2000,  2:  1609-1611 
  • 5j See further: Wender PA. Barzilay CM. Dyckman AJ. J. Am. Chem. Soc.  2001,  123:  179-180 
  • 6a [4+4] Cycloaddition reactions: Wender PA. Ihle NC. J. Am. Chem. Soc.  1986,  108:  4678 -4679
  • 6b See also: Wender PA. Tebbe MJ. Synthesis  1991,  1089-1094 
  • 6c [6+2] Cycloaddition reactions: Wender PA. Correa AG. Sato Y. Sun R. J. Am. Chem. Soc.  2000,  122:  7815-7816 
  • 6d [5+2+1] Cycloaddition reactions: Wender PA. Gamber GG. Hubbard RD. Zhang L. J. Am. Chem. Soc.  2002,  124:  2876-2877 
  • 7a Kuntz EG. CHEMTECH  1987,  17:  570 -575
  • 7b Driessenholscher B. Adv. Catal.  1998,  42:  473 -505
  • 8a Nearest known examples include [(DPPE tetra sodium sulfonate)Rh(cod)Cl]: Amrani Y. Lecomte L. Sinou D. Organometallics  1989,  8:  542 -547
  • 8b {[(S,S)-chiraphos tetra sodium sulfonate]Rh(H2O)2}+: Bartik T. Bunn BB. Bartik B. Hanson BE. Inorg. Chem.  1994,  33:  164-169 ; and compounds described therewith
  • 10 Fairlie DP. Bosnich B. Organometallics  1988,  7:  936 -945
  • 11 Gilbertson SR. Hoge GS. Genov DG. J. Org. Chem.  1998,  63:  10077 -10080
9

Commercially available from Strem Chemicals: $121.00 for 1 g, catalog # 15-0155.