Rh-N-heterocyclic carbene (NHC) complex-catalyzed addition of phenylboronie acid to N-sulfonyl and N-phosphinoyl aldimines

Chemical and Pharmaceutical Bulletin

Volumn 56, Issue 7, 2008, Pages 973-976

  Md , Abu Bakar ^a   Suzuki, Yumiko ^a   Sato, Masayuki ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

Addition reaction; N heterocyclic carbene; N phosphinoylarylimine; N sulfonylarylimine; Phenylboronie acid; Rhodium

Indexed keywords

BENZENEBORONIC ACID; CARBENE; DIOXANE; IMIDAZOLE DERIVATIVE; IMINE; N PHOSPHINOYL ALDIMINE; N SULFONYL ALDIMINE;

ADDITION REACTION; ARTICLE; ARYLATION; CATALYSIS; CATALYST; COMPLEX FORMATION; REACTION ANALYSIS;

BORONIC ACIDS; CATALYSIS; HETEROCYCLIC COMPOUNDS; IMINES; METHANE;

EID: 46749091295     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.56.973     Document Type: Article

References (42)

1. Arduengo A. J., III, Harlow R. L., Kline M. A., J . Am. Chem. Soc., 113, 361-363 (1991).
2. Herrrmann W. A., Angew. Chem. Int. Ed., 41, 1290-1309 (2002).
3. Crudden C. M., Allen D. P., Coord. Chem. Rev., 248, 2247-2273 (2004).
4. Perris E., Crabtree R. H., Coord. Chem. Rev., 248, 2239-2246 (2004).
5. Gurbuz N., Ozdemir Y., Cetinkaya B., Tetrahedron Lett., 46, 2273-2277 (2005).
6. Burling S., Whittlesey M. K., Williams J. M., J . Adv. Synth. Catal., 347, 591-594 (2005).
7. Hillier A. C., Grasa G. A., Viciu M. S., Lee H. M., Yang C., Nolan S. P., J. Organomet. Chem., 653, 69-82 (2002).
8. Ender D., Gielen H., J. Organomet. Chem., 617, 618, 70-80 (2001).
9. Lappert M. F., Maskell R. K., J. Organomet. Chem., 264, 217-228 (1984).
10. Herrrmann W. A., Goosen L. J., Kocher C., Artus G. R. J., Angew. Chem. Int. Ed., 35, 2805-2807 (1996).
11. Gade L. H., Cesar V., Bellemin-Laponaz S., Angew. Chem. Int. Ed., 43, 1014-1017 (2004).
12. Fraser P. K., Woodward S., Tetrahedron Lett., 42, 2747-2749 (2001).
13. Guillen F., Winn C. L., Alexakis A., Tetrahedron: Asymmetry, 12, 2083-2086 (2001).
14. Pytkowicz J., Roland S., Mangeney P., Tetrahedron: Asymmetry, 12, 2087-2089 (2001).
15. Ukai T., Tanaka R., Dokawa S., J. Pharm. Soc. Jpn., 63, 296-300 (1943).
16. Ukai T., Dokawa T., Tsubokawa S., J. Pharm. Soc. Jpn., 64, 3-4 (1944).
17. Breslow R., J. Am. Chem. Soc., 80, 3719-3726 (1958).
18. Breslow R., McNeils E., J. Am. Chem. Soc., 81, 3080-3082 (1959).
19. Miyashita A., Suzuki Y., Iwamoto K., Higashino T., Chem. Pharm. Bull., 42, 2633-2635 (1994).
20. Miyashita A., Suzuki Y., Kobayashi M., Kuriyama N., Higashino T., Heterocycles, 43, 509-512 (1996).
21. Stetter H., Angew. Chem., 88, 695-704 (1976).
22. Stetter H., Kuhlmann H., Chem. Ber., 109, 2890-2896 (1976).
23. Stetter H., Kuhlmann H., Org. React., 40, 407-496 (1991).
24. Grasa G. A., Kissling R. M., Nolan S. P., Org. Lett., 4, 3583-3586 (2002).
25. Nyce G. W., Lamboy J. A., Connor E. F., Waymouth R. M., Hedrick L., Org. Lett., 4, 3587-3590 (2002).
26. Miyashita A., Obae K., Suzuki Y., Iwamoto K., Oishi E., Higashino T., Heterocycles, 45, 2159-2173 (1997).
27. Miyashita A., Suzuki Y., Iwamoto K., Oishi E., Higashino T., Heterocycles, 49, 405-413 (1998).
28. Miyashita A., Suzuki Y., Iwamoto K., Higashino T., Chem. Pharm. Bull., 46, 390-399 (1998).
29. Md. A. B., Suzuki Y., Sato M., Chem. Pharm. Bull., 56, 57-59 (2008).
30. Calderon S. N., Rothman R. B., Porreca F., Flippen-Anderson J. L., McNutt R. W., Xu H., Smith L. E., Bilsky E. J., Davis P., Rice K., J. Med. Chem., 37, 2125-2128 (1994).
31. Delorme D., Berthellete C., Lavoie R., Roberts E., Tetrahedron: Asymmetry, 9, 3963-3966 (1998).
32. Cottney J., Rankovic Z., Morphy R., J . Bioorg. Med. Chem. Lett., 9, 1329-1334 (1999).
33. Plobech N., Powel D., Tetrahedron: Asymmetry, 13, 303-310 (2002).
34. Kuriyama M., Soeta T., Hao X., Chen Q., Tomioka K., J. A m . Chem. Soc., 126, 8128-8129 (2004).
35. Weix D. J., Shi Y., Ellman J. A., J. Am. Chem. Soc., 127, 1092-1093 (2005).
36. Legault C. L., Kendall C., Charette A. B., Chem. Commun., 2005, 3826-3828 (2005).
37. Fürstner A., Krause H., Adv. Synth. Catal., 343, 343-350 (2001).
38. Lee K. Y., Lee C. G., Kim J. N., Tetrahedron Lett., 44, 1231-1234 (2003).
39. Jennings W. B., Lovely C. J., Tetrahedron, 47, 5561-5568 (1991).
40. Oi S., Moro M., Fukuhara H., Kawanishi T., Inoue Y., Tetrahedron, 59, 4351-4361 (2003).
41. Wang Z.-Q., Feng C.-G., Xu M.-H., Lin G.-Q., J. Am. Chem. Soc., 129, 5336-5337 (2007).
42. Almansa R., Guijarro D., Yus M., Tetrahedron, 63, 1167-1174 (2006).