Synthesis and reactivity of aryl- and heteroaryl-magnesium reagents bearing keto groups

Synlett

Volumn , Issue 11, 2002, Pages 1799-1802

  Kneisel, Florian Felix ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Cross coupling; Functionalised organomagnesium reagents; Iodine magnesium exchange; Palladium catalysis

Indexed keywords

KETONE DERIVATIVE; MAGNESIUM DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; REAGENT;

ARTICLE; CATALYSIS; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 0036418005     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34865     Document Type: Article

References (17)

1. (a) Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem. Int. Ed. 2000, 39, 4415.
2. (b) Knochel, P.; Millot, N.; Rodriguez, A. L.; Tucker, C. E. Organic Reactions, Vol. 58; Overman, L. E., Ed.; Wiley & Sons Ltd.: New York, 2001, 417.
3. Jensen, A. E.; Dohle, W.; Sapountzis, I.; Lindsay, D. M.; Vu, V. A.; Knochel, P. Synthesis 2002, 565.
4. (a) Alexakis, A.; Malan, C.; Lea, L.; Benhaim, C.; Fournioux, X. Synlett 2001, 927.
5. (b) Yuan, T.-M.; Yeh, S.-M.; Hsieh, Y.-T.; Luh, T.-Y. J. Org. Chem. 1994, 59, 8192.
6. (c) Tuckmantel, W.; Oshima, K.; Nozaki, H. Chem. Ber. 1986, 119, 1581.
7. (d) Tamura, M.; Kochi, J. K. Bull. Chem. Soc. Jpn. 1971, 44, 3063.
8. Villieras, J.; Rambaud, M. Synthesis 1982, 11, 924.
9. Takahashi, Y.; Ito, T.; Sakai, S.; Ishii, Y. Chem. Comm. 1970, 1065.
10. Allen, D. W.; Hurley, B. G.; Mellor, M. T. J. J. Chem. Soc., Perkin Trans. 2 1972, 63.
11. (a) Negishi, E. Acc. Chem. Res. 1982, 15, 340.
12. (b) Negishi, E.; Valente, L. F.; Kobayashi, M. J. Am. Chem. Soc. 1980, 102, 3298.
13. (c) Kobayashi, M.; Negishi, E. J. Org. Chem. 1980, 45, 5223.
14. (d) Tamaru, Y.; Ochiai, H.; Nakamura, T.; Yoshida, Z. Tetrahedron Lett. 1986, 27, 955.
15. (e) Klement, I.; Rottländer, M.; Tucker, C. E.; Majid, T. N.; Knochel, P.; Venegas, P.; Cahiez, G. Tetrahedron 1996, 52, 7201.
16. Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390.
17. 4Cl (5 mL). The aqueous phase was extracted with dichloromethane (3 × 30 mL) and the combined organic phases were dried with sat. aq NaCl and concentrated in vacuo. The residue was purified by flash chromatography (95:5 pentane/ethyl acetate), yielding 1-(5-trimethylstannylthiophen-2-yl)-butan-1-one (13) as a clear liquid (190 mg, 60%).