Internal aryl-aryl coupling reaction using a novel and highly active palladium reagent prepared from Pd(OAc)2, DPPP, and Bu3P

Chemical and Pharmaceutical Bulletin

Volumn 45, Issue 10, 1997, Pages 1723-1725

  Harayama, Takashi ^a   Akiyama, Toshihiko ^a   Nakano, Yuichiro ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Aryl halide arene coupling; Aryl triflate arene coupling; Bidentate ligand; Internal biaryl coupling; Pd reagent

Indexed keywords

BENZO[C]PHENANTHRIDINE DERIVATIVE; CHELERYTHRINE; PALLADIUM; PALLADIUM COMPLEX; PROPANE; SANGUINARINE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; HYDROLYSIS;

EID: 0030709351     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.45.1723     Document Type: Article

References (23)

1. a) Simanek V., "The Alkaloids," Vol. 26, ed. by Brossi A., Academic Press. Inc., New York, 1983, pp 185-240;
2. b) Dostal J., Potacek M., Collect. Czech. Chem. Commun., 55, 2840-2873 (1990).
3. Herert J. M., Augereau J. M., Gleye J., Maffrand J. P., Biophys. Res. Commun., 172, 993-999 (1990).
4. Fang S.-D., Wang L.-K., Hecht S. M., J. Org. Chem., 58, 5025-5027 (1993).
5. a) Vavreckova C., Gawlik I., Muller K., Planta Med., 62, 397-401 (1995);
6. b) Idem, ibid., 62, 491-494 (1996);
7. c) Schmeller T., Latz-Bruning B., Wink M., Phytochemistry, 44, 257-266 (1997).
8. a) J. Tsuji, "Palladium Reagents and Catalysts," John Wiley & Sons Inc., New York, 1995, pp. 125-252;
9. b) D. W. Knight, "Comprehensive Organic Synthesis," Vol. 3, ed. by B. M. Trost, I. Fleming, Pergamon Press, Oxford, 1991, pp. 481-520.
10. Harayama T., Akiyama T., Kawano K., Chem. Pharm. Bull., 44, 1634-1636 (1996).
11. 2 gave 8a in 94% yield.
12. Black M., Cadogan J.I.G., McNab H., J. Chem Soc., Perkin Trans. 1, 1994, 155-159.
13. Hosoya T., Takashiro E., Matsumoto T., and Suzuki k., J. Am. Chem. Soc., 116, 1004 (1994).
14. a) Tolman C. A., Chem. Rev., 97, 313-348 (1977);
15. b) Steffen W. L., Palenik G. J., Inorg. Chem., 15, 2432-2438 (1976).
16. a) Dolle R. E., Schmidt S. J., Kruse L. I., J. Chem. Soc., Chem. Commun., 1987, 904-905 and refereces cited therein;
17. b) Cabri W., Candiani I., Acc. Chem. Res., 28, 2-7 (1995);
18. c) Cabri W., Candiani I., DeBemardinis S., Francalanci F., Penco S., J. Org. Chem., 56, 5796-5800 (1991).
19. Mandai T., Matsumoto T., Tsuji J., Tetrahedron Lett., 34, 2513-2516 (1993).
20. 2O with a total yield of 48%.
21. 2O with a total yield of 43%.
22. a) Katritzky A. R., Black M., Fan W.-Q., J. Org. Chem., 56, 5045-5048 (1991);
23. b) Johnstone R. A. W., Payling D. W., Thomas C., J. Chem. Soc., (C), 1969, 2223-2224.