Palladium(0)-catalyzed carbonylation on the Multipin(TM) system

Tetrahedron Letters

Volumn 40, Issue 44, 1999, Pages 7843-7846

  Takahashi, Takashi ^a   Inoue, Hitoshi ^a   Tomida, Satoshi ^a   Doi, Takayuki ^a   Bray, Andrew M ^b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b Migenix Inc   (United States)

Author keywords

Amides; Aryl halides; Carbonylation; Esters; Palladium catalysts; Solid phase synthesis

Indexed keywords

ALCOHOL DERIVATIVE; AMIDE; AMINE; AMINO ACID DERIVATIVE; CARBON MONOXIDE; ESTER; IODIDE; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; SOLID; SYNTHESIS;

EID: 0033615760     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01667-6     Document Type: Article

References (21)

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2. 1. Schoenberg, A.; Bartoletti, I.; Heck, R. F. J. Org. Chem. 1974, 39, 3318-3326; Schoenberg, A.; Heck, R. F. J. Org. Chem. 1974, 39, 3327-3331; Hidai, M.; Hikita, T.; Wada, Y.; Fujikura, Y.; Uchida, Y. Bull. Chem. Soc. Jpn. 1975, 48, 2075-2077; Ito, T.; Mori, K.; Mizoroki, T.; Ozaki, A. Bull. Chem. Soc. Jpn. 1975, 48, 2091-2094; Stille, J. K.; Wong, P. K. J. Org. Chem. 1975, 40, 532-534.
3. 1. Schoenberg, A.; Bartoletti, I.; Heck, R. F. J. Org. Chem. 1974, 39, 3318-3326; Schoenberg, A.; Heck, R. F. J. Org. Chem. 1974, 39, 3327-3331; Hidai, M.; Hikita, T.; Wada, Y.; Fujikura, Y.; Uchida, Y. Bull. Chem. Soc. Jpn. 1975, 48, 2075-2077; Ito, T.; Mori, K.; Mizoroki, T.; Ozaki, A. Bull. Chem. Soc. Jpn. 1975, 48, 2091-2094; Stille, J. K.; Wong, P. K. J. Org. Chem. 1975, 40, 532-534.
4. 1. Schoenberg, A.; Bartoletti, I.; Heck, R. F. J. Org. Chem. 1974, 39, 3318-3326; Schoenberg, A.; Heck, R. F. J. Org. Chem. 1974, 39, 3327-3331; Hidai, M.; Hikita, T.; Wada, Y.; Fujikura, Y.; Uchida, Y. Bull. Chem. Soc. Jpn. 1975, 48, 2075-2077; Ito, T.; Mori, K.; Mizoroki, T.; Ozaki, A. Bull. Chem. Soc. Jpn. 1975, 48, 2091-2094; Stille, J. K.; Wong, P. K. J. Org. Chem. 1975, 40, 532-534.
5. 1. Schoenberg, A.; Bartoletti, I.; Heck, R. F. J. Org. Chem. 1974, 39, 3318-3326; Schoenberg, A.; Heck, R. F. J. Org. Chem. 1974, 39, 3327-3331; Hidai, M.; Hikita, T.; Wada, Y.; Fujikura, Y.; Uchida, Y. Bull. Chem. Soc. Jpn. 1975, 48, 2075-2077; Ito, T.; Mori, K.; Mizoroki, T.; Ozaki, A. Bull. Chem. Soc. Jpn. 1975, 48, 2091-2094; Stille, J. K.; Wong, P. K. J. Org. Chem. 1975, 40, 532-534.
6. 2. Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: Tokyo 1995, pp 188-209.
7. 3. Takahashi, T.; Nagashima, T.; Tsuji, J. Chem. Lett. 1980, 369-372; Takahashi, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1980, 21, 3885-3888.
8. 3. Takahashi, T.; Nagashima, T.; Tsuji, J. Chem. Lett. 1980, 369-372; Takahashi, T.; Ikeda, H.; Tsuji, J. Tetrahedron Lett. 1980, 21, 3885-3888.
9. 4. For the rhodium-catalyzed asymmetric hydrogenation of polymer-supported dehydropeptides, see: Ojima, I.; Tsai, C.-Y.; Zhang, Z., Tetrahedron Lett. 1994, 35, 5785-5788.
10. 5. Takahashi, T.; Ebata, S.; Doi, T. Tetrahedron Lett. 1998, 39, 1369-1372.
11. 6. For Multipin approach, see: Valerio, R. M.; Bray, A. M.; Maeji, N. J., Int. J. Peptide Protein Res. 1994, 44, 158-165; Virgilio, A. A.; Ellman, J. A., J. Am. Chem. Soc. 1994, 116, 11580-11581; Valerio, R. M.; Bray, A. M.; Patsiouras, H., Tetrahedron Lett. 1996, 37, 3019-3022; Gilbertson, S. R.; Wang, X., Tetrahedron Lett. 1996, 37, 6475-6478; Rodebaugh, R.; Joshi, S.; Fraser-Reid, B.; Geysen, H. M., J. Org. Chem. 1997, 62, 5660-5661; Takahashi, T.; Tomida, S.; Inoue, H.; Doi T. Synlett 1998, 1261-1263.
12. 6. For Multipin approach, see: Valerio, R. M.; Bray, A. M.; Maeji, N. J., Int. J. Peptide Protein Res. 1994, 44, 158-165; Virgilio, A. A.; Ellman, J. A., J. Am. Chem. Soc. 1994, 116, 11580-11581; Valerio, R. M.; Bray, A. M.; Patsiouras, H., Tetrahedron Lett. 1996, 37, 3019-3022; Gilbertson, S. R.; Wang, X., Tetrahedron Lett. 1996, 37, 6475-6478; Rodebaugh, R.; Joshi, S.; Fraser-Reid, B.; Geysen, H. M., J. Org. Chem. 1997, 62, 5660-5661; Takahashi, T.; Tomida, S.; Inoue, H.; Doi T. Synlett 1998, 1261-1263.
13. 6. For Multipin approach, see: Valerio, R. M.; Bray, A. M.; Maeji, N. J., Int. J. Peptide Protein Res. 1994, 44, 158-165; Virgilio, A. A.; Ellman, J. A., J. Am. Chem. Soc. 1994, 116, 11580-11581; Valerio, R. M.; Bray, A. M.; Patsiouras, H., Tetrahedron Lett. 1996, 37, 3019-3022; Gilbertson, S. R.; Wang, X., Tetrahedron Lett. 1996, 37, 6475-6478; Rodebaugh, R.; Joshi, S.; Fraser-Reid, B.; Geysen, H. M., J. Org. Chem. 1997, 62, 5660-5661; Takahashi, T.; Tomida, S.; Inoue, H.; Doi T. Synlett 1998, 1261-1263.
14. 6. For Multipin approach, see: Valerio, R. M.; Bray, A. M.; Maeji, N. J., Int. J. Peptide Protein Res. 1994, 44, 158-165; Virgilio, A. A.; Ellman, J. A., J. Am. Chem. Soc. 1994, 116, 11580-11581; Valerio, R. M.; Bray, A. M.; Patsiouras, H., Tetrahedron Lett. 1996, 37, 3019-3022; Gilbertson, S. R.; Wang, X., Tetrahedron Lett. 1996, 37, 6475-6478; Rodebaugh, R.; Joshi, S.; Fraser-Reid, B.; Geysen, H. M., J. Org. Chem. 1997, 62, 5660-5661; Takahashi, T.; Tomida, S.; Inoue, H.; Doi T. Synlett 1998, 1261-1263.
15. 6. For Multipin approach, see: Valerio, R. M.; Bray, A. M.; Maeji, N. J., Int. J. Peptide Protein Res. 1994, 44, 158-165; Virgilio, A. A.; Ellman, J. A., J. Am. Chem. Soc. 1994, 116, 11580-11581; Valerio, R. M.; Bray, A. M.; Patsiouras, H., Tetrahedron Lett. 1996, 37, 3019-3022; Gilbertson, S. R.; Wang, X., Tetrahedron Lett. 1996, 37, 6475-6478; Rodebaugh, R.; Joshi, S.; Fraser-Reid, B.; Geysen, H. M., J. Org. Chem. 1997, 62, 5660-5661; Takahashi, T.; Tomida, S.; Inoue, H.; Doi T. Synlett 1998, 1261-1263.
16. 6. For Multipin approach, see: Valerio, R. M.; Bray, A. M.; Maeji, N. J., Int. J. Peptide Protein Res. 1994, 44, 158-165; Virgilio, A. A.; Ellman, J. A., J. Am. Chem. Soc. 1994, 116, 11580-11581; Valerio, R. M.; Bray, A. M.; Patsiouras, H., Tetrahedron Lett. 1996, 37, 3019-3022; Gilbertson, S. R.; Wang, X., Tetrahedron Lett. 1996, 37, 6475-6478; Rodebaugh, R.; Joshi, S.; Fraser-Reid, B.; Geysen, H. M., J. Org. Chem. 1997, 62, 5660-5661; Takahashi, T.; Tomida, S.; Inoue, H.; Doi T. Synlett 1998, 1261-1263.
17. 7. Rink, H. Tetrahedron Lett. 1987, 28, 3787-3790; Rink amine crowns were prepared from Fmoc-NH-Rink-Polystyrene crowns by treatment with 20% piperidine in DMF for 20 min before use. Batch no. 810-1, Loading = 9.5 μmol per crown, Chiron Technologies Pty. Ltd.
18. 8. DIC = diisopropylcarbodiimide, HOBt = 1-hydroxybenzotriazole
19. 3(100 μL), and aryl halides (0.5 M) in DMF (1.0 mL) were added, respectively. The tubes were placed in an autoclave, which was purged with carbon monoxide three times before applying a pressure of 15 atm. After being left at 80 °C for 12 h, the acylated crowns 7 (or 3) were consecutively washed with DMF (3 times), dichloromethane (twice), DMF (twice), acetonitrile (twice), 50% acetonitrile in water (4 times), methanol (3 times), and dichloromethane (3 times) and dried in vacuo. The cleavage was performed by treatment with 95% trifluoroacetic acid (TFA) in water for 1 h. The crude products were subjected to HPLC and mass spectral analyses.
20. 10. Double carbonylation was detected on iodobenzene systems with electron-donating substituents. This result is identical with that reported in an elegant work of double carbonylation; see, Ozawa, F.; Soyama, H.; Yanagihara, H.; Aoyama, I.; Takino, H.; Izawa, K.; Yamamoto, T.; Yamamoto, A. J. Am. Chem. Soc. 1985, 107, 3235-3245.
21. 11. For a recent report of double carbonylation, see: Couve-Bonnaire, S.; Carpentier, J.-F.; Castanet, Y.; Mortreux, A. Tetrahedron Lett. 1999, 40, 3717-3718.