Palladium-imidazolium-catalyzed carbonylative coupling of aryl diazonium ions and aryl boronic acids

Tetrahedron Letters

Volumn 43, Issue 50, 2002, Pages 9137-9140

  Andrus, Merritt B ^a   Ma, Yudao ^b   Zang, Yunfu ^b   Song, Chun ^a  

^a Brigham Young University   (United States)

^b SHANDONG UNIVERSITY   (China)

Author keywords

Arylboronic acid; Aryldiazonium; Carbonylative; Catalysis; Imidazolium; Ketone; Palladium

Indexed keywords

BORONIC ACID DERIVATIVE; CARBONYL DERIVATIVE; DIAZONIUM COMPOUND; IMIDAZOLE DERIVATIVE; KETONE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHROMATOGRAPHY; ELECTRON TRANSPORT; STOICHIOMETRY; TEMPERATURE;

EID: 0037049168     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02186-X     Document Type: Article

References (21)

1. Miyaura N., Suzuki A. Chem. Rev. 95:1995;2457-2483.
2. Echavarren A.M., Stille J.K. J. Am. Chem. Soc. 110:1988;1557-1565.
3. Kang S.-K., Yamaguchi T., Kim T.-H., Ho P.-S. J. Org. Chem. 61:1996;9082-9083.
4. Morera E., Ortar G. Bioorg. Med. Chem. Lett. 10:2000;1815-1818.
5. Ceccarelli S., Piarulli U., Gennari C. J. Org. Chem. 65:2000;6254-6256.
6. Yamamoto M., Kohara T., Yamamoto A. Chem. Lett. 1976;1217-1220.
7. Bumagin N.A., Ponomaryov A.B., Beletskaya I.P. Tetrahedron Lett. 26:1985;4819-4822.
8. Hatanaka Y., Fukushima S., Hiyama T. Tetrahedron. 48:1992;2113-2119.
9. Ishiyama T., Kizaki H., Suzuki A., Miyaura N. Tetrahedron Lett. 34:1993;7595-7598.
10. Ishiyama T., Kizaki H., Hayashi T., Suzuki A., Miyaura N. J. Org. Chem. 63:1998;4726-4731.
11. Skoda-Földes R., Székvölgi Z., Kollár L., Berente Z., Horváth J., Tuba Z. Tetrahedron. 56:2000;3415-3418.
12. Andrus M.B., Song C. Org. Lett. 3:2001;3761-3764.
13. Andrus M.B., Song C., Zhang J. Org. Lett. 4:2002;2079-2082.
14. Grasa G.A., Nolan S.P. Org. Lett. 3:2001;119-122.
15. Huang J., Grasa G., Nolan S.P. Org. Lett. 1:1999;1307-1309.
16. Huang J., Nolan S.P. J. Am. Chem. Soc. 121:1999;9889-9890.
17. Yang C., Lee H.M., Nolan S.P. Org. Lett. 3:2001;1511-1514.
18. Zhang C., Huang J., Trudell M.L., Nolan S.P. J. Org. Chem. 64:1999;3804-3805.
19. An autoclave with a pressure gauge was used.
20. Aryl diazonium ions were formed using the procedure of: Doyle M.P., Siegfreid B., Elliot R.C., Dellaria J.F. J. Org. Chem. 42:1977;2431.
21. 3): δ 7.21-7.77 (m, 13H), 6.79 (d, 1H, J=6.8); MS (EI) m/z 258.