Alkynyl sulfides as dienophiles in cobalt-catalyzed Diels-Alder reactions

Synthesis

Volumn , Issue 12, 2003, Pages 1784-1786

  Hilt, Gerhard ^a   Lüers, Steffen ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Alkynes; Catalysis; Cobalt; Diels Alder reactions; Sulfides

Indexed keywords

CATALYSIS; OXIDATION; SUBSTITUTION REACTIONS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

CYCLOADDITION;

ADDITION REACTIONS;

ALKADIENE; COBALT; DIENOPHILE DERIVATIVE; SULFIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; ENVIRONMENTAL TEMPERATURE; OXIDATION;

EID: 0141742508     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41034     Document Type: Article

References (12)

1. For reviews concerning alkynyl sulfoxides and alkynyl sulfones as dienophiles in Diels-Alder reactions, see: (a) Lee, A. W. M.; Chan, W. H. Top. Curr. Chem. 1997, 190, 103. (b) Lee, A. W. M.; Chan, W. H.; Zhang, H. K.; Xia, P. F. Curr. Org. Chem. 2003, 7, 573.
2. For reviews concerning alkynyl sulfoxides and alkynyl sulfones as dienophiles in Diels-Alder reactions, see: (a) Lee, A. W. M.; Chan, W. H. Top. Curr. Chem. 1997, 190, 103. (b) Lee, A. W. M.; Chan, W. H.; Zhang, H. K.; Xia, P. F. Curr. Org. Chem. 2003, 7, 573.
3. (a) Sauer, J.; Heldmann, D. K.; Hetzenegger, J.; Krauthan, J.; Sichert, H.; Schuster, J. Eur. J. Org. Chem. 1998, 2885.
4. (b) Nakayama, J.; Yamaoka, S.; Nakanishi, T.; Hoshino, M. J. Am. Chem. Soc. 1988, 110, 6598.
5. For recent cobalt(I)-catalysed Diels-Alder reactions with functionalised non-activated starting materials, see: (a) Hilt, G.; Smolko, K. I. Angew. Chem. Int. Ed. 2003, 43, 2797; Angew. Chem. 2003, 115, 2901. (b) Hilt, G.; Smolko, K. I. Synthesis 2002, 686. (c) Hilt, G.; Smolko, K. I. Synlett 2002, 1081.
6. For recent cobalt(I)-catalysed Diels-Alder reactions with functionalised non-activated starting materials, see: (a) Hilt, G.; Smolko, K. I. Angew. Chem. Int. Ed. 2003, 43, 2797; Angew. Chem. 2003, 115, 2901. (b) Hilt, G.; Smolko, K. I. Synthesis 2002, 686. (c) Hilt, G.; Smolko, K. I. Synlett 2002, 1081.
7. For recent cobalt(I)-catalysed Diels-Alder reactions with functionalised non-activated starting materials, see: (a) Hilt, G.; Smolko, K. I. Angew. Chem. Int. Ed. 2003, 43, 2797; Angew. Chem. 2003, 115, 2901. (b) Hilt, G.; Smolko, K. I. Synthesis 2002, 686. (c) Hilt, G.; Smolko, K. I. Synlett 2002, 1081.
8. Small amounts of reduction products, such as alkenyl sulfides, were detected by GC-MS analysis.
9. For the synthesis of alkyl alkynyl sulfides, see: (a) Voets, M.; Smet, M.; Dehaen, W. J. Chem. Soc., Perkin Trans 1 1999, 1473. (b) Woodgate, P. D.; Sutherland, H. S.; Rickard, C. E. F. J. Organomet. Chem. 2001, 627, 206.
10. For the synthesis of alkyl alkynyl sulfides, see: (a) Voets, M.; Smet, M.; Dehaen, W. J. Chem. Soc., Perkin Trans 1 1999, 1473. (b) Woodgate, P. D.; Sutherland, H. S.; Rickard, C. E. F. J. Organomet. Chem. 2001, 627, 206.
11. For the synthesis of aryl alkynyl sulfides, see: (a) Maruyama, H.; Shiozaki, M.; Oida, S.; Hiraoka, T. Tetrahedron Lett. 1985, 26, 4521. (b) Kabanyane, S. T.; MaGee, D. I. Can J. Chem. 1992, 70, 2758.
12. For the synthesis of aryl alkynyl sulfides, see: (a) Maruyama, H.; Shiozaki, M.; Oida, S.; Hiraoka, T. Tetrahedron Lett. 1985, 26, 4521. (b) Kabanyane, S. T.; MaGee, D. I. Can J. Chem. 1992, 70, 2758.