Electrophilic ipso-iodination of silylated arylboronic acids

Journal of Organometallic Chemistry

Volumn 695, Issue 24, 2010, Pages 2635-2643

  Durka, K ^a   Gorka J ^a   Kurach, P ^a   Lulinski S ^a   Serwatowski, J ^a  

^a WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Arylborinic compounds; Arylboronic acids; Arylsilanes; Electrophilic ipso substitution; Iodination; Suzuki cross coupling

Indexed keywords

ARYLBORINIC COMPOUNDS; ARYLBORONIC ACIDS; ARYLSILANES; ELECTROPHILIC IPSO-SUBSTITUTION; IODINATION; SUZUKI CROSS COUPLING;

CHEMICAL REACTIONS; CHLORINE COMPOUNDS; ESTERS; IODINE;

ACIDS;

EID: 77957763711     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2010.08.016     Document Type: Article

References (31)

1. O. Baron, and P. Knochel Angew. Chem. Int. Ed. 44 2005 3133 3135
2. C.C. Caires, and S. Guccione Organometallics 27 2008 747 752
3. R.M. Al-Zoubi, O. Marion, and D.G. Hall Angew. Chem. Int. Ed. 47 2008 2876 2879
4. H.G. Kuivila, and L.E. Benjamin J. Am. Chem. Soc. 77 1955 4834 4836
5. M. Dbrowski, P. Kurach, S. Luliński, and J. Serwatowski Appl. Organomet. Chem. 21 2007 234 238
6. P. Kurach, S. Luliński, and J. Serwatowski Eur. J. Org. Chem. 2008 3171 3178
7. K. Durka, P. Kurach, S. Luliński, and J. Serwatowski Eur. J. Organomet. Chem. 2009 4325 4332
8. R.L. Funk, and K.P.C. Vollhardt J. Chem. Soc. Chem. Commun. 1976 833 834
9. S. Luliński, and K. Zajc J. Org. Chem. 73 2008 7785 7788
10. S. Luliński, I. Madura, J. Serwatowski, H. Szatyłowicz, and J. Zachara New J. Chem 31 2007 144 154
11. M.T. Ashby, and N.A. Sheshtawy Organometallics 13 1994 236 243
12. K.J. Weese, R.A. Bartlett, B.D. Murray, M.M. Olmstead, and P. Power Inorg. Chem. 26 1987 2409 2413
13. S.M. Cornet, K.B. Dillon, C.D. Entwistle, M.A. Fox, A.E. Goeta, H.P. Goodwin, T.B. Marder, and A.L. Thompson Dalton Trans. 2003 4395 4405
14. A.D. Becke J. Chem. Phys. 98 1993 1372 1377
15. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
16. R. Krishnan, J.S. Binkley, R. Seeger, and J.A. Pople J. Chem. Phys. 72 1980 650 654
17. P.R. Mallinson, G.T. Smith, C.C. Wilson, E. Grech, and K. Woźniak J. Am. Chem. Soc. 125 2003 4259 4270
18. G. Manickam, and A.D. Schlüter Eur. J. Org. Chem. 2000 3475 3481
19. E. Hupe, M.I. Calaza, and P. Knochel Chem. Commun. 2002 1390 1391
20. A. Del Zotto, F. Amoroso, W. Baratta, and P. Rigo Eur. J. Org. Chem. 2009 110 116
21. E.K. Perttu, M. Arnold, and P.M. Iovine Tetrahedron Lett. 46 2005 8753 8756
22. A.L. Korich, and P.M. Iovine Dalton Trans. 39 2010 1423 1431
23. S. Luliński, and J. Serwatowski J. Org. Chem. 68 2003 9384 9388
24. G.J. Chen, and Christ Tamborski J. Org. Chem. 251 1983 149 158
25. M. Schlosser, F. Cottet, C. Heiss, O. Lefebvre, M. Marull, E. Masson, and R. Scopelliti Eur. J. Org. Chem. 2006 729 734
26. APEX2, Bruker AXS. SAINT, ver. 7.60A (within APEX2 program package). Bruker AXS. (2008) Madison, Wisconsin, USA.
27. G.M. Sheldrick Acta Cryst. A64 2008 112 122
28. H. Fuess, International Tables for Crystallography first ed. Mathematical, Physical and Chemical Tables vol. C 2006 International Union of Crystallography Chester
29. M.J. Frisch, G.W. Truck, H.B. Schlegel, G.E. Scuseria, M.A. Robb, and J.R. Cheeseman Gaussian 03, Revision E.01 2004 Gaussian, Inc. Wallingford CT
30. R.F.W. Bader Atoms in Molecules - A Quantum Theory 1990 Oxford University Press Oxford
31. F. Biegler-König, J. Schönbohm, and D.J. Bayles J. Comput. Chem. 22 2001 545 559