Pure Appl. Chem., 2010, Vol. 82, No. 7, pp. 1393-1402
http://dx.doi.org/10.1351/PAC-CON-09-09-22
Published online 2010-05-04
Mechanism of the oxidative addition of aryl halides to bis-carbene palladium(0) complexes
References
- 1a. J. F. J. Organomet. Chem. 208, 419 (1981). ( , F. Pflüger, M. Troupel. http://dx.doi.org/10.1016/S0022-328X(00)86726-1)
- 1b. C. Organometallics 9, 2276 (1990). ( , F. Pflüger. http://dx.doi.org/10.1021/om00158a026)
- 1c. C. Organometallics 12, 3168 (1993). ( , A. Jutand, F. Khalil, M. A. M’Barki, L. Mottier. http://dx.doi.org/10.1021/om00032a045)
- 2. For Pd0(PPh3)3 generated as the major complex from Pd0(PPh3)4, see.
- 2a. B. E. J. Chem. Soc., Dalton Trans. 1673 (1975). ( , A. Musco. http://dx.doi.org/10.1039/dt9750001673)
- 2b. J. J. Chem. Soc., Dalton Trans. 2207 (2002). ( , L. O’Neill, V. L. Kambhampati, G. Rayner, S. Turin, A. Genge, A. J. Dent, T. Neisius. http://dx.doi.org/10.1039/b200617k)
- 3. Reaction rate = k[Pd0L2][ArX] = kK[Pd0L3][ArX]/[L] = kapp[Pd0L3][ArX].
- 4. A. Organometallics 14, 1810 (1995). ( , A. Mosleh. http://dx.doi.org/10.1021/om00004a038)
- 5a. J. F. J. Am. Chem. Soc. 117, 5373 (1995). ( , F. Paul. http://dx.doi.org/10.1021/ja00124a026)
- 5b. F. J. Am. Chem. Soc. 127, 6944 (2005). ( , J. F. Hartwig. http://dx.doi.org/10.1021/ja042959i)
- 5c. F. J. Am. Chem. Soc. 131, 8141 (2009). ( , B. P. Carrow, J. F. Hartwig. http://dx.doi.org/10.1021/ja900798s)
- 6. E. Angew. Chem., Int. Ed. 41, 1760 (2002). ( , S. Ramdeehul, J. M. Brown, A. Cowley, K. K. Hii, A. Jutand. http://dx.doi.org/10.1002/1521-3773(20020517)41:10<1760::AID-ANIE1760>3.0.CO;2-3)
- 7. R. B. Organometallics 26, 4763 (2007). ( . http://dx.doi.org/10.1021/om7003223)
- 8. W. A. Angew. Chem., Int. Ed., 34, 2371 (1995). ( , M. Elison, J. Fischer, C. Köcher, G. R. J. Artus. http://dx.doi.org/10.1002/ange.19951072004)
- 9. For reviews, see.
- 9a. W. A. Angew. Chem., Int. Ed. Engl. 36, 2162 (1997). ( , C. Köcher. http://dx.doi.org/10.1002/anie.199721621)
- 9b. W. A. Angew. Chem., Int. Ed. 41, 1290 (2002). ( . http://dx.doi.org/10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO;2-Y)
- 9c. A. C. J. Organomet. Chem. 653, 69 (2002). ( , G. A. Grasa, M. S. Viciu, H. M. Lee, C. Yang, S. P. Nolan. http://dx.doi.org/10.1016/S0022-328X(02)01154-3)
- 9d. W. A. J. Organomet. Chem. 687, 229 (2003). ( , K. Öfele, D. V. Preysing, S. Schneider. http://dx.doi.org/10.1016/j.jorganchem.2003.07.028)
- 9e. K. J. Coord. Chem. Rev. 248, 671 (2004). ( , D. S. McGuinness. http://dx.doi.org/10.1016/j.ccr.2004.02.006)
- 9f. V. Adv. Synth. Catal. 346, 1553 (2004). ( . http://dx.doi.org/10.1002/adsc.200404178)
- 9g. N. M. Eur. J. Inorg. Chem. 1815 (2005). ( , S. P. Nolan. http://dx.doi.org/10.1002/ejic.200500030)
- 9h. F. Tetrahedron 61, 11771 (2005). ( , I. P. Beletskaya, M. Yus. http://dx.doi.org/10.1016/j.tet.2005.08.054)
- 9i. F. Tetrahedron 64, 3047 (2008). ( , I. P. Beletskaya, M. Yus. http://dx.doi.org/10.1016/j.tet.2007.12.036)
- 10. J. J. Organomet. Chem. 678, 166 (2003). ( , S. Roland, P. Mangeney, G. Meyer, A. Jutand. http://dx.doi.org/10.1016/S0022-328X(03)00476-5)
- 11. A. K. de K. J. Am. Chem. Soc. 125, 10066 (2003). ( , S. Caddick, F. G. N. Cloke, N. C. Billingham, P. B. Hitchcock, J. Leonard. http://dx.doi.org/10.1021/ja035565k)
- 12. S. Synlett 3088 (2006). , P. Mangeney, A. Jutand.
- 13. D. Chem. Rev. 100, 39 (2000). ( , O. Guerret, F. P. Gabbaï, G. Bertrand. http://dx.doi.org/10.1021/cr940472u)
- 14. P. L. Organometallics 18, 3228 (1999). ( , F. G. N. Cloke, T. Geldbach, P. B. Hitchcock. http://dx.doi.org/10.1021/om990224u)
- 15. For a review on the use of electrochemistry to solve mechanistic problems in transition-metal-catalyzed reactions, see: A. Chem. Rev. 108, 2300 (2008). ( . http://dx.doi.org/10.1021/cr068072h)
- 16. For the technique used to determine the absolute number n of electron(s) involved in any electrochemical process, see ref. [15] and: C. J. Electroanal. Chem. 288, 45 (1990). ( , M. Azzabi, P. Calas, A. Jutand, C. Lefrou, Y. Rollin. http://dx.doi.org/10.1016/0022-0728(90)80024-Z)
- 17a. A. J. Org. Chem. 62, 261 (1997). ( , A. Mosleh. http://dx.doi.org/10.1021/jo961464b)
- 17b. C. Organometallics 12, 3168 (1993). ( , A. Jutand, F. Khalil, M. A. M’Barki, L. Mottier. http://dx.doi.org/10.1021/om00032a045)
- 18. In agreement with.
- 18a. R. J. Am. Chem. Soc. 127, 2485 (2005). ( , E. D. Stevens, N. M. Scott, C. Costabile, L. Cavallo, C. D. Hoff, S. P. Nolan. http://dx.doi.org/10.1021/ja0438821)
- 18b. S. Coord. Chem. Rev. 251, 874 (2007). ( , S. P. Nolan. http://dx.doi.org/10.1016/j.ccr.2006.10.004)
- 19. A. J. J. Am. Chem. Soc. 116, 6641 (1994). ( III, H. Bock, H. Chen, M. Denk, D. A. Dixon, J. C. Green, W. A. Herrmann, N. L. Jones, M. Wagner, R. West. http://dx.doi.org/10.1021/ja00094a020)
- 20. S. Chem.—Eur. J. 10, 3072 (2004). ( , S. Shaik, A. Jutand, C. Amatore. http://dx.doi.org/10.1002/chem.200306056)