Three roles for the fluoride ion in palladium-catalyzed hiyama reactions: Transmetalation of [ArPdFL2] by Ar'Si(OR)3

Angewandte Chemie - International Edition

Volumn 53, Issue 27, 2014, Pages 6982-6985

  Amatore, Christian ^a   Grimaud, Laurence ^a   Le Duc, Gaëtan ^a   Jutand, Anny ^a  

^a CNRS   (France)

Author keywords

cross coupling; fluoride; kinetics; palladium; reaction mechanisms

Indexed keywords

CATALYSIS; ENZYME KINETICS; FLUORINE COMPOUNDS; KINETICS; PALLADIUM; REACTION KINETICS; SILICATES; SILICON;

ANTAGONISTIC EFFECTS; CROSS-COUPLINGS; ELECTROCHEMICAL TECHNIQUES; FLUORIDE; PALLADIUM-CATALYZED; REACTION MECHANISM; REDUCTIVE ELIMINATION; TRANSMETALATION;

REACTION INTERMEDIATES;

EID: 84903206513     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201400956     Document Type: Article

References (24)

1. Y. Hatanaka, T. Hiyama, Tetrahedron Lett. 1988, 29, 97-98
2. K.-i. Gouda, E. Hagiwara, Y. Hatanaka, T. Hiyama, J. Org. Chem. 1996, 61, 7232-7233
3. K. Shibata, K. Miyazawa, Y. Goto, Chem. Commun. 1997, 1309-1310
4. E. Mowery, P. DeShong, Org. Lett. 1999, 1, 2137-2140
5. H. M. Lee, S. P. Nolan, Org. Lett. 2000, 2, 2053-2055
6. G. A. Molander, L. Iannazzo, J. Org. Chem. 2011, 76, 9182-9187
7. Y. Hatanaka, T. Hiyama, Synlett 1991, 845-853
8. T. Hiyama, E. Shirakawa, Organosilicon Compounds in Topics in Current Chemistry, Vol. 219, Springer, Berlin 2002, pp. 61-85.
9. Y. Hatanaka, K.-i. Goda, Y. Okahara, T. Hiyama, Tetrahedron 1994, 50, 8301-8316
10. Y. Hatanaka, T. Hiyama, J. Am. Chem. Soc. 1990, 112, 7793-7794
11. A. Sugiyama, Y.-y. Ohnishi, M. Nakaoka, Y. Nakao, H. Sato, S. Sakaki, Y. Nakao, T. Hiyama, J. Am. Chem. Soc. 2008, 130, 12975-12985.
12. S. E. Denmark, D. Wehrli, Org. Lett. 2000, 2, 565-568
13. S. E. Denmark, R. F. Sweis, D. Wehrli, J. Am. Chem. Soc. 2004, 126, 4865-4875
14. S. E. Denmark, C. Regens, Acc. Chem. Res. 2008, 41, 1486-1499
15. S. E. Denmark, J. H. C. Liu, Angew. Chem. 2010, 122, 3040-3049
16. Angew. Chem. Int. Ed. 2010, 49, 2978-2986.
17. C. Amatore, A. Jutand, G. Le Duc, Angew. Chem. 2012, 124, 2542-2545
18. Angew. Chem. Int. Ed. 2012, 51, 2492-2503
19. C. Amatore, A. Jutand, G. Le Duc, Chem. Eur. J. 2013, 19, 10082-10093.
20. 2], see:, M. C. Pilon, V. V. Grushin, Organometallics 1998, 17, 1774-1781.
21. 2], see:, C. Adamo, C. Amatore, I. Ciofini, A. Jutand, H. Lakmini, J. Am. Chem. Soc. 2006, 128, 6829-6836.
22. R. Giovannini, P. Knochel, J. Am. Chem. Soc. 1998, 120, 11186-11187
23. A. G. Jarvis Amanda, I. J. S. Fairlamb, Curr. Org. Chem. 2011, 15, 3175-3196.
24. K. C. Kumara Swany, V. Chandrasekhar, J. J. Harland, J. M. Holmes, R. O. Day, R. R. Holmes, J. Am. Chem. Soc. 1990, 112, 2341-2348.