Room temperature cross-coupling of highly functionalized organozinc reagents with thiomethylated N-heterocycles by nickel catalysis

Journal of Organic Chemistry

Volumn 75, Issue 6, 2010, Pages 2131-2133

  Melzig, Laurin ^a   Metzger, Albrecht ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTHIAZOLES; BENZYLIC; CATALYTIC SYSTEM; CHEMICAL EQUATIONS; CROSS COUPLING REACTIONS; CROSS-COUPLINGS; FUNCTIONALIZED; ISOQUINOLINES; N-HETEROCYCLES; NI(ACAC)2; NICKEL CATALYSIS; ORGANOZINC REAGENTS; PYRAZINES; QUINAZOLINES; ROOM TEMPERATURE; ZINC REAGENTS;

CHEMICAL BONDS; HYDROCARBONS; ORGANOMETALLICS; ZINC;

CHEMICAL REACTIONS;

(3 PENTANOYLBENZYL)ZINC CHLORIDE; 2 (3 PENTANOYLBENZYL)NICOTINONITRILE; 2 (METHYLTHIO) 1,3 BENZOXAZOLE; 2 (METHYLTHIO)NICOTINONITRILE; 3 ETHOXYCARBONYLPHENYLZINC IODIDE; 4 (2 FURYL) 2 METHYLTHIO 6 TRIFLUOROMETHYLPYRIMIDINE; 4 CYANOPROPYLZINC BROMIDE; 4 ETHOXYCARBONYLPHENYLZINC IODIDE; 4 FLUOROBENZYLZINC CHLORIDE; 6,7 DIMETHOXY 4 (METHYLTHIO)QUINAZOLINE; BENZOTHIAZOLE DERIVATIVE; BENZOXAZOLE DERIVATIVE; ISOQUINOLINE DERIVATIVE; NICKEL; PYRAZINE DERIVATIVE; PYRIDAZINE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; QUINAZOLINE DERIVATIVE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE;

EID: 77949807925     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1001615     Document Type: Article

References (27)

1. (a) Okamura, H.; Miura, M.; Takei, H. Tetrahedron Lett. 1979, 1, 43.
2. (b) Wenkert, E.; Ferreira, T. W.; Michelotti. E. L. J. Chem. Soc, Chem. Commun. 1979, 637.
3. (c) Wenkert, E.; Ferreira, T. W. J. Chem. Soc. Chem. Commun. 1982, 840.
4. (d) Wenkert, E.; Shepard, M. E.; McPhail, A. T. J. Chem. Soc., Chem. Commun. 1986, 1390.
5. Srogl, J.; Liu, W.; Marshall, D.; Liebeskmd, L. S. J. Am. Chem. Soc. 1999, 121, 9449.
6. Lee, K.; Counceller, C. M.; Stambuli, J. P. Org. Lett. 2009, 11, 1457.
7. Metzger, A.; Melzig, L.; Despotopoulou, C.; Knochel, P. Org. Lett. 2009, 11, 4228.
8. Itami, K.; Higashi, S.; Mineno, M.; Yoshida, J.-i. Org. Lett. 2005, 7, 1219.
9. Angiolelli, M. E.; Casalnuovo, A. L.; Selby, T. P. Synlett 2000, 905.
10. (a) Knochel, P.; Millot, N. Rodriguez, A. L.; Tucker, C. E. Org. React. 2001, 58, 417
11. (b) Knochel, P.; Leuser, H.; Gong, L.-Z.; Perrone, S.; Kneisel, F. F. Handbook of Functionalized Organometallics; Knochel, P., Ed.; Wiley-VCH: Weinheim, 2005; Vol.1, p 251.
12. (c) Manolikakes, G.; Munoz Hernandez, C.; Schade, M. A.; Metzger, A.; Knochel, P. J. Org. Chem. 2008, 73, 8422.
13. (d) Metzger, A.; Schade, M. A.; Knochel, P. Org. Lett. 2008, 10, 1107.
14. (e) Dong, Z.; Clososki, G. C.; Wunderlich, S. H.; Unsinn, A.; Li, J.; Knochel, P. Chem.-Eur. J. 2009, 15, 457.
15. (f) Mosrin, M.; Monzon, G.; Bresser, T.; Knochel, P. Chem. Comnrnn. 2009, 37, 5615.
16. (g) Piller, F. M.; Metzger, A.; Schade, M. A.; Haag, B. A.; Gavryushin, A.; Knochel, P. Chem.- Eur. J. 2009, 15, 7192.
17. we have also verified that the pyridine moiety does not act as a ligand.
18. Miyaura, N.; Tanabe, Y.; Suginome, H.; Suzuki, A. J. Organomet. Chem. 1982, 233, C 13.
19. Gonzalez-Bobes, F.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 5360.
20. Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; Goubitz, K.; Fraanje, J.; van Leeuwen, P. W. N. M. Organomettallics 1995, 14, 3081.
21. Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymettry 1993, 4, 743.
22. Hamann, B. C. Hartwig, J. F. J. Am. Chem. Soc. 1998, 20, 7369.
23. Arduengo, A. J. III; Rasika Dias, H. V.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530.
24. Melzig, L.; Gavryushin, A.; Knochel, P. Org. Lett. 2007, 9, 5529.
25. 2 to 2.5 mol Vo to decrease the reaction time especially in the case of unreactive zinc reagents such as 5j or 51.
26. All aryl- and alkylzinc reagents were prepared according to Krasovskiy, A.; Malakhov, V.; Gavryushin, A.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 6040.
27. All benzylic zinc reagents were prepared according to Metzger, A.; Schade, M. A.; Manolikakes, G.; Knochel, P. Chem. Asian. J. 2008, 3, 1678.