Organic synthesis in ionic liquids: The stille coupling

Organic Letters

Volumn 3, Issue 2, 2001, Pages 233-236

  Handy, Scott T ^a   Zhang, Xiaolei ^a  

^a BINGHAMTON UNIVERSITY   (United States)

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ARTICLE;

EID: 0000532907     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0068849     Document Type: Article

References (22)

1. For a recent review, see: Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Sausalito, CA, 1999.
2. For a review of the Stille reaction, see: Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652.
3. For example, coupling reactions of aryl chlorides generally fail to afford any of the desired product. However, the biphenylphosphine ligands reported by Buchwald have extended the scope of Suzuki and siloxane couplings to encompass aryl chlorides as well as hindered aryl bromides. For examples, see: Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550. Mowery, M. E.; DeShong, P. Org. Lett. 1999, 1, 2137.
4. For example, coupling reactions of aryl chlorides generally fail to afford any of the desired product. However, the biphenylphosphine ligands reported by Buchwald have extended the scope of Suzuki and siloxane couplings to encompass aryl chlorides as well as hindered aryl bromides. For examples, see: Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550. Mowery, M. E.; DeShong, P. Org. Lett. 1999, 1, 2137.
5. For a recent volume discussing alternate solvents and reagent recycling, see: Modern Solvents in Organic Synthesis; Knochel, P., Ed.; Topics in Current Chemistry, Vol. 206; Springer-Verlag: Berlin, 1999.
6. For a recent review, see: Welton, T.; Chem. Rev. 2000, 100, 2071-2083.
7. For examples utilizing this approach not included in ref 5, see the following. Asymmetric epoxidation: Song, C. E.; Rho, E. J. Chem. Commun. 2000, 837-838. Heck reaction: Bohm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2000, 6, 1017-1025. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 997. Friedel-Crafts alkylation: Song, C. E.; Shim, W. H.; Roh, E. J.; Choi, J. H. Chem. Commun. 2000, 1695. Oxidation of aldehydes: Howarth, J. Tetrahedron Lett. 2000, 41, 6627. Hydrogenations: Steines, S.; Wasserscheid, P.; Driessen-Hoelscher, B. J. Prakt. Chem. 2000, 342, 348. Suzuki reaction: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Trost-Tsuji Reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
8. For examples utilizing this approach not included in ref 5, see the following. Asymmetric epoxidation: Song, C. E.; Rho, E. J. Chem. Commun. 2000, 837-838. Heck reaction: Bohm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2000, 6, 1017-1025. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 997. Friedel-Crafts alkylation: Song, C. E.; Shim, W. H.; Roh, E. J.; Choi, J. H. Chem. Commun. 2000, 1695. Oxidation of aldehydes: Howarth, J. Tetrahedron Lett. 2000, 41, 6627. Hydrogenations: Steines, S.; Wasserscheid, P.; Driessen-Hoelscher, B. J. Prakt. Chem. 2000, 342, 348. Suzuki reaction: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Trost-Tsuji Reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
9. For examples utilizing this approach not included in ref 5, see the following. Asymmetric epoxidation: Song, C. E.; Rho, E. J. Chem. Commun. 2000, 837-838. Heck reaction: Bohm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2000, 6, 1017-1025. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 997. Friedel-Crafts alkylation: Song, C. E.; Shim, W. H.; Roh, E. J.; Choi, J. H. Chem. Commun. 2000, 1695. Oxidation of aldehydes: Howarth, J. Tetrahedron Lett. 2000, 41, 6627. Hydrogenations: Steines, S.; Wasserscheid, P.; Driessen-Hoelscher, B. J. Prakt. Chem. 2000, 342, 348. Suzuki reaction: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Trost-Tsuji Reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
10. For examples utilizing this approach not included in ref 5, see the following. Asymmetric epoxidation: Song, C. E.; Rho, E. J. Chem. Commun. 2000, 837-838. Heck reaction: Bohm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2000, 6, 1017-1025. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 997. Friedel-Crafts alkylation: Song, C. E.; Shim, W. H.; Roh, E. J.; Choi, J. H. Chem. Commun. 2000, 1695. Oxidation of aldehydes: Howarth, J. Tetrahedron Lett. 2000, 41, 6627. Hydrogenations: Steines, S.; Wasserscheid, P.; Driessen-Hoelscher, B. J. Prakt. Chem. 2000, 342, 348. Suzuki reaction: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Trost-Tsuji Reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
11. For examples utilizing this approach not included in ref 5, see the following. Asymmetric epoxidation: Song, C. E.; Rho, E. J. Chem. Commun. 2000, 837-838. Heck reaction: Bohm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2000, 6, 1017-1025. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 997. Friedel-Crafts alkylation: Song, C. E.; Shim, W. H.; Roh, E. J.; Choi, J. H. Chem. Commun. 2000, 1695. Oxidation of aldehydes: Howarth, J. Tetrahedron Lett. 2000, 41, 6627. Hydrogenations: Steines, S.; Wasserscheid, P.; Driessen-Hoelscher, B. J. Prakt. Chem. 2000, 342, 348. Suzuki reaction: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Trost-Tsuji Reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
12. For examples utilizing this approach not included in ref 5, see the following. Asymmetric epoxidation: Song, C. E.; Rho, E. J. Chem. Commun. 2000, 837-838. Heck reaction: Bohm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2000, 6, 1017-1025. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 997. Friedel-Crafts alkylation: Song, C. E.; Shim, W. H.; Roh, E. J.; Choi, J. H. Chem. Commun. 2000, 1695. Oxidation of aldehydes: Howarth, J. Tetrahedron Lett. 2000, 41, 6627. Hydrogenations: Steines, S.; Wasserscheid, P.; Driessen-Hoelscher, B. J. Prakt. Chem. 2000, 342, 348. Suzuki reaction: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Trost-Tsuji Reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
13. For examples utilizing this approach not included in ref 5, see the following. Asymmetric epoxidation: Song, C. E.; Rho, E. J. Chem. Commun. 2000, 837-838. Heck reaction: Bohm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2000, 6, 1017-1025. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 997. Friedel-Crafts alkylation: Song, C. E.; Shim, W. H.; Roh, E. J.; Choi, J. H. Chem. Commun. 2000, 1695. Oxidation of aldehydes: Howarth, J. Tetrahedron Lett. 2000, 41, 6627. Hydrogenations: Steines, S.; Wasserscheid, P.; Driessen-Hoelscher, B. J. Prakt. Chem. 2000, 342, 348. Suzuki reaction: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Trost-Tsuji Reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
14. For examples utilizing this approach not included in ref 5, see the following. Asymmetric epoxidation: Song, C. E.; Rho, E. J. Chem. Commun. 2000, 837-838. Heck reaction: Bohm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2000, 6, 1017-1025. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 997. Friedel-Crafts alkylation: Song, C. E.; Shim, W. H.; Roh, E. J.; Choi, J. H. Chem. Commun. 2000, 1695. Oxidation of aldehydes: Howarth, J. Tetrahedron Lett. 2000, 41, 6627. Hydrogenations: Steines, S.; Wasserscheid, P.; Driessen-Hoelscher, B. J. Prakt. Chem. 2000, 342, 348. Suzuki reaction: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Trost-Tsuji Reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
15. For examples utilizing this approach not included in ref 5, see the following. Asymmetric epoxidation: Song, C. E.; Rho, E. J. Chem. Commun. 2000, 837-838. Heck reaction: Bohm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2000, 6, 1017-1025. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 997. Friedel-Crafts alkylation: Song, C. E.; Shim, W. H.; Roh, E. J.; Choi, J. H. Chem. Commun. 2000, 1695. Oxidation of aldehydes: Howarth, J. Tetrahedron Lett. 2000, 41, 6627. Hydrogenations: Steines, S.; Wasserscheid, P.; Driessen-Hoelscher, B. J. Prakt. Chem. 2000, 342, 348. Suzuki reaction: Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249. Aza-Diels-Alder reaction: Zulfiqar, F.; Kitazume, T. Green Chem. 2000, 137. Trost-Tsuji Reaction: Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E. Green Chem. 2000, 149.
16. This concept was introduced by Chauvin and co-workers and emulated in many of the studies cited in refs 5 and 6. For this initial communication, see: Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem., Int. Ed. Engl. 1994, 34, 2698.
17. Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W. Tetrahedron Lett. 1992, 33, 919-922.
18. 4 acting as a more polar solvent.
19. 4 acting as a more polar solvent.
20. 6 derivative (Huddleston, J. G.; Willauer, H. D.; Swarloski, R. P.; Visser, A. E.; Rogers, R. D. Chem. Commun. 1998, 1765). Details may be found in the Supporting Information.
21. 4 and was immediately lowered into an oil bath maintained at 80 °C. To this solution was added 0.35 mL (1.200 mmol) of tributylvinyltin. After stirring for 2 h, the reaction mixture was extracted with diethyl ether (10 × 10 mL). The combined organic layers were washed with saturated aqueous potassium fluoride (3 × 30 mL) The aqueous layers were combined and back-extracted with diethyl ether (2 × 20 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting oily residue was purified by flash column chromatography (5:95, then 1.9 EtOAc/Hexanes as eluent) to afford 90.3 mg (82%) of 3-methyl-2-vinylcyclohexenone as a pale yellow oil.
22. All compounds exhibited spectral data consistent with that reported in the literature.