TMPZnOPiv•LiCl: A new base for the preparation of air-stable solid zinc pivalates of sensitive aromatics and heteroaromatics

Organic Letters

Volumn 15, Issue 6, 2013, Pages 1302-1305

  Stathakis, Christos I ^a   Manolikakes, Sophia M ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84875207257     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400242r     Document Type: Article

References (34)

1. Knochel, P.; Almena, J.; Jones, P. Tetrahedron 1998, 54, 8275
2. Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4115
3. Knochel, P.; Leuser, H.; Cong, L.-Z.; Perrone, S.; Kneisel, F. F. Handbook of Functionalized Organometallics; Knochel, P., Ed.; Wiley-VCH: Weinheim, Germany, 2005; p 251.
4. Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390
5. Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117
6. Negishi, E.; Valente, L. F.; Kobayashi, M. J. Am. Chem. Soc. 1980, 102, 3298
7. Erdik, E. Tetrahedron 1992, 48, 9577
8. Bernhardt, S.; Manolikakes, G.; Kunz, T.; Knochel, P. Angew. Chem., Int. Ed. 2011, 50, 9205
9. Stathakis, C. I.; Bernhardt, S.; Quint, V.; Knochel, P. Angew. Chem., Int. Ed. 2012, 51, 9428
10. Kondo, Y.; Shilai, H.; Uchiyama, M.; Sakamoto, T. J. Am. Chem. Soc. 1999, 121, 3539
11. Imahori, T.; Uchiyama, M.; Kondo, Y. Chem. Commun. 2001, 2450
12. Schwab, P. F. H.; Fleischer, F.; Michl, J. J. Org. Chem. 2002, 67, 443
13. Uchiyama, M.; Miyoshi, T.; Kajihara, Y.; Sakamoto, T.; Otami, Y.; Ohwada, T.; Kondo, Y. J. Am. Chem. Soc. 2002, 124, 8514
14. Uchiyama, M.; Matsumoto, Y.; Nobuto, D.; Furuyama, T.; Yamaguchi, K.; Morokuma, K. J. Am. Chem. Soc. 2006, 128, 8748
15. Clegg, W.; Dale, S. H.; Drummond, A. M.; Hevia, E.; Honeyman, G. W.; Mulvey, R. E. J. Am. Chem. Soc. 2006, 128, 7434
16. Hevia, E.; Honeyman, G. W.; Mulvey, R. E. J. Am. Chem. Soc. 2005, 127, 13106
17. Armstrong, D. R.; Clegg, W.; Dale, S. H.; Hevia, E.; Hogg, L. M.; Honeyman, G. W.; Mulvey, R. E. Angew. Chem., Int. Ed. 2006, 45, 3775
18. Wunderlich, S. H.; Knochel, P. Angew. Chem., Int. Ed. 2007, 46, 7685
19. Wunderlich, S. H.; Knochel, P. Org. Lett. 2008, 10, 4705
20. Mosrin, M.; Knochel, P. Chem.-Eur. J. 2009, 15, 1468
21. Mosrin, M.; Knochel, P. Org. Lett. 2009, 11, 1837
22. Mosrin, M.; Monzon, G.; Bresser, T.; Knochel, P. Chem. Commun. 2009, 5615
23. Bresser, T.; Mosrin, M.; Monzon, G.; Knochel, P. J. Org. Chem. 2010, 75, 4686
24. Bresser, T.; Knochel, P. Angew. Chem., Int. Ed. 2011, 50, 1914
25. Duez, S.; Steib, A.; Manolikakes, S. M.; Knochel, P. Angew. Chem., Int. Ed. 2011, 50, 7686
26. Negishi, E.; King, A. O.; Okukado, N. J. Org. Chem. 1977, 42, 1821
27. Wang, G.; Yin, N.; Negishi, E. Chem.-Eur. J. 2011, 17, 4118
28. Negishi, E.; Zeng, X.; Tan, Z.; Qian, M.; Hu, Q.; Huang, Z. Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 815.
29. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585
30. Klement, I.; Rottlander, M.; Tucker, C. E.; Majid, T. N.; Knochel, P.; Venegas, P.; Cahiez, G. Tetrahedron 1996, 52, 7201
31. Alkenyl iodide 7i was prepared in 87% yield according to the procedure described in: Krishnamurthy, V. R.; Dougherty, A.; Haller, C. A.; Chaikof, E. L. J. Org. Chem. 2011, 76, 5543
32. Klier, L.; Bresser, T.; Nigst, T. A.; Karaghiosoff, K.; Knochel, P. J. Am. Chem. Soc. 2012, 134, 13584
33. Duez, S.; Steib, A.; Knochel, P. Org. Lett. 2012, 14, 1951
34. Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 127, 4685