Cross-couplings of alkyl halides with heteroaromatic halides, in water at room temperature

Tetrahedron Letters

Volumn 52, Issue 17, 2011, Pages 2203-2205

  Krasovskiy, Arkady ^a   Thomé, Isabelle ^a   Graff, Julien ^a   Krasovskaya, Valeria ^a   Konopelski, Paul ^a   Duplais, Christophe ^a   Lipshutz, Bruce H ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Green chemistry; Heteroaromatic halides; Micellar catalysis; Negishi like cross coupling; Pd catalysis

Indexed keywords

AMPHOPHILE; CARBON; HALIDE; PALLADIUM; WATER; ZINC;

ARTICLE; CATALYST; CROSS COUPLING REACTION; MICELLE; ROOM TEMPERATURE;

EID: 79953169089     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.160     Document Type: Article

References (33)

1. (a) Netherton, M. R.; Fu, G. C. Adv. Synth. Catal. 2004, 346, 1525;
2. (b) Terao, J.; Kambe, N. Acc. Chem. Res. 2008, 41, 1545;
3. (c) Sherry, B. D.; Fürstner, A. Acc. Chem. Res. 2008, 41, 1500;
4. (d) Frisch, A.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674;
5. (e) Rudolph, A.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 2656;
6. (f) Nakamura, M.; Ito, S. In Modern Arylation Methods; Ackermann, L., Ed.; Wiley; Weinheim, 2009;
7. (g) Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. J. Org. Chem. 2005, 70, 8503;
8. (h) Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Org. Lett. 2005, 7, 3805;
9. (i) Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Angew. Chem., Int. Ed. 2006, 45, 3656;
10. (j) Organ, M. G.; Avola, S.; Dubovyk, I.; Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Valente, C. Chem. Eur. J. 2006, 12, 4749.
11. (a) Cahiez, G.; Avedissian, H. Synthesis 1998, 1199;
12. (b) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856;
13. (c) Fürstner, A.; Leitner, A. Angew. Chem., Int. Ed. 2002, 41, 609;
14. (d) Martin, R.; Fürstner, A. Angew. Chem., Int. Ed. 2004, 43, 3955;
15. (e) Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 3686;
16. (f) Nagano, T.; Hayashi, T. Org. Lett. 2004, 6, 1297;
17. (g) Bedford, R. B.; Bruce, D. W.; Frost, R.; Hird, M. Chem. Commun. 2005, 4161;
18. (h) Nakamura, M.; Ito, S.; Matsuo, K.; Nakamura, E. Synlett 2005, 126, 1794;
19. (i) Bedford, R. B.; Betham, M.; Bruce, D. W.; Danopoulos, A. A.; Frost, R.; Hird, M. J. Org. Chem. 2006, 71, 1104;
20. (j) Cahiez, G.; Habiak, V.; Duplais, C.; Moyeux, A. Angew. Chem., Int. Ed. 2007, 46, 4364;
21. (k) Cahiez, G.; Duplais, C.; Moyeux, A. Org. Lett. 2007, 9, 3253;
22. (l) Czaplik, W. M.; Mayer, M.; von Wangelin, J. Angew. Chem., Int. Ed. 2009, 48, 607.
23. (a) Knochel, P.; Leuser, H.; Gong, L.-Z.; Perone, S.; Kneisel, F. F. In Handbook of Functionalized Organometallics; Knochel, P., Ed.; Wiley; Weinheim, 2005;
24. (b) Krasovskiy, A.; Malakhov, V.; Gavryushin, A.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 6040.
25. Lipshutz, B. H.; Abela, A. R. Org. Lett. 2008, 10, 5329.
26. Lipshutz, B. H.; Ghorai, S. Aldrichim. Acta 2008, 41, 59.
27. Krasovskiy, A.; Duplais, C.; Lipshutz, B. H. J. Am. Chem. Soc. 2009, 131, 15592.
28. Lipshutz, B. H.; Taft, B. R. Org. Lett. 2008, 10, 1329.
29. Lipshutz, B. H.; Petersen, T. B.; Abela, A. R. Org. Lett. 2008, 10, 1333.
30. (a) Lipshutz, B. H.; Aguinaldo, G. T.; Ghorai, S.; Voigtritter, K. R. Org. Lett. 2008, 10, 1325;
31. (b) Lipshutz, B. H.; Ghorai, S.; Aguinaldo, G. T. Adv. Synth. Catal. 2008, 350, 953.
32. Chichibabin, A. E.; Zeide, O. A. Zr. Russ. Fiz. Khim. Obshch. 1914, 46, 1212.
33. Alternatively, the reaction mixture was diluted with ethyl acetate and diethyl ether and filtered through a plug of silica gel. Silica gel was additionally washed with 100 mL of ethyl acetate and 100 mL diethyl ether. Organic solvents were removed in vacuo and product was isolated by column chromatography.