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Synlett 2003(9): 1295-1298
DOI: 10.1055/s-2003-40357
DOI: 10.1055/s-2003-40357
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York
Rhodium-Catalyzed [5+2] Cycloaddition Reactions in Water
Further Information
Received
17 December 2003
Publication Date:
30 June 2003 (online)
Publication History
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.
Key words
water-soluble catalyst - biphasic reactions - cycloaddition - medium-sized rings - rhodium
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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
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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 -
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2g
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2h
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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
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4a
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4b
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4c
Wender PA.Smith TE. Tetrahedron 1998, 54: 1255-1275 - Intramolecular [5+2] reactions:
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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
References
Commercially available from Strem Chemicals: $121.00 for 1 g, catalog # 15-0155.