Catalysis; Electrochemistry; Olefins; Radicals and radical reactions; Ruthenium and compounds
Abstract :
[en] [RuCl2(p-cymene)] complexes containing triarylphosphine ligands with various substituents at the para position were used to catalyse the atom transfer radical addition of carbon tetrachloride to various olefins, and their catalytic activities were nicely correlated with their electrochemical parameters.
K. Matyjaszewski, and J. Xia Chem. Rev. 101 2001 2921 2990
M. Kamigaito, T. Ando, and M. Sawamoto Chem. Rev. 101 2001 3689 3745
A.J. Clark Chem. Soc. Rev. 31 2002 1 11
R.A. Gossage, L.A. van de Kuil, and G. van Koten Acc. Chem. Res. 31 1998 423 431
F. Simal, A. Demonceau, and A.F. Noels S.G. Pandalai Recent Research Developments in Organic Chemistry Vol. 3 1999 Transworld Research Network Trivandrum 455 464
L. Delaude, A. Demonceau, and A.F. Noels Top. Organomet. Chem. 11 2004 155 171
H. Matsumoto, T. Nakano, and Y. Nagai Tetrahedron Lett. 14 1973 5147 5150
F. Simal, S. Sebille, A. Demonceau, A.F. Noels, R. Núñez, M. Abad, F. Teixidor, and C. Viñas Tetrahedron Lett. 41 2000 5347 5351
O. Tutusaus, C. Viñas, R. Núñez, F. Teixidor, A. Demonceau, S. Delfosse, A.F. Noels, I. Mata, and E. Molins J. Am. Chem. Soc. 125 2003 11830 11831
O. Tutusaus, S. Delfosse, A. Demonceau, A.F. Noels, C. Viñas, and F. Teixidor Tetrahedron Lett. 44 2003 8421 8425
J.A. Tallarico, L.M. Malnick, and M.L. Snapper J. Org. Chem. 64 1999 344 345
F. Simal, A. Demonceau, and A.F. Noels Tetrahedron Lett. 40 1999 5689 5693
F. Simal, L. Wlodarczak, A. Demonceau, and A.F. Noels Tetrahedron Lett. 41 2000 6071 6074
F. Simal, L. Wlodarczak, A. Demonceau, and A.F. Noels Eur. J. Org. Chem. 2001 2689 2695
R.A. Zelonka, and M.C. Baird Can. J. Chem. 50 1972 3063 3072
M.A. Bennett, and A.K. Smith J. Chem. Soc., Dalton Trans. 1974 233 241
F. Simal, A. Demonceau, and A.F. Noels Angew. Chem. 111 1999 559 562
Angew. Chem., Int. Ed. 38 1999 538 540
F. Simal, L. Delaude, D. Jan, A. Demonceau, and A.F. Noels Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 40 1999 336 337
F. Simal, D. Jan, A. Demonceau, and A.F. Noels K. Matyjaszewski Controlled/Living Radical Polymerization: Progress in ATRP, NMP, and RAFT ACS Symposium Series 768 2000 American Chemical Society Washington, DC 223 233
F. Simal, S. Sebille, L. Hallet, A. Demonceau, and A.F. Noels Macromol. Symp. 161 2000 73 85
F. Simal, D. Jan, L. Delaude, A. Demonceau, M.-R. Spirlet, and A.F. Noels Can. J. Chem. 79 2001 529 535
L. Quebatte, M. Haas, E. Solari, R. Scopelliti, Q.T. Nguyen, and K. Severin Angew. Chem., Int. Ed. 44 2005 1084 1088
L. Quebatte, E. Solari, R. Scopelliti, and K. Severin Organometallics 24 2005 1404 1406
L. Quebatte, R. Scopelliti, and K. Severin Eur. J. Inorg. Chem. 2005 3353 3358
N.Q. Méndez, J.W. Seyler, A.M. Arif, and J.A. Gladysz J. Am. Chem. Soc. 115 1993 2323 2334
J.W. Faller, J.T. Nguyen, W. Ellis, and M.R. Mazzieri Organometallics 12 1993 1434 1438
T.V. RajanBabu, T.A. Ayers, and A.L. Casalnuovo J. Am. Chem. Soc. 116 1994 4101 4102
A.L. Casalnuovo, T.V. RajanBabu, T.A. Ayers, and T.H. Warren J. Am. Chem. Soc. 116 1994 9869 9882
C. Babij, H. Chen, L. Chen, and A.J. Poë Dalton Trans. 2003 3184 3191
For examples of the use of electrochemistry in transition-metal-catalysed reactions, see: C. Amatore, M. Azzabi, and A. Jutand J. Am. Chem. Soc. 113 1991 8375 8384
Y. Na, C. Lee, J.Y. Pak, K.H. Lee, and S. Chang Tetrahedron Lett. 45 2004 7863 7865
For examples of the use of electrochemistry in ATRP, see: J. Qiu, K. Matyjaszewski, L. Thouin, and C. Amatore Macromol. Chem. Phys. 201 2000 1625 1631
K. Matyjaszewski, B. Göbelt, H.-J. Paik, and C.P. Horwitz Macromolecules 34 2001 430 440
L. Delaude, S. Delfosse, A. Richel, A. Demonceau, and A.F. Noels Chem. Commun. 2003 1526 1527
A. Richel, O. Tutusaus, C. Viñas, F. Teixidor, A. Demonceau, and A.F. Noels Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 46 2005 227 228
For similar pKa-redox potential correlations, see: Md. M. Rahman, H.-Y. Liu, K. Eriks, A. Prock, and W.P. Giering Organometallics 8 1989 1 7
K. Wohnrath, A.A. Batista, A.G. Ferreira, J. Zukerman-Schpector, L.A. de Oliveira, and E.E. Castellano Polyhedron 17 1998 2013 2020
C.H. Suresh, and N. Koga Inorg. Chem. 41 2002 1573 1578
Cyclic voltammetry experiments were conducted at room temperature with a Princeton Applied Research EG & G 236 A potentiostat, using a conventional three-electrode configuration consisting of a 3 mm diameter glassy carbon working electrode, a platinum auxiliary electrode and an Ag/AgCl/saturated KCl reference electrode. Tetrabutylammonium hexafluorophosphate was used as the supporting electrolyte and all the potentials were referenced to ferrocene, E0(Fc/Fc+) = 0.0 V, added at the end of the experiment.
