Abstract
Six rhodium–carbene complexes (2a–f) have been prepared and the new compounds characterized by C, H, N analyses, 1H-n.m.r. and 13C-n.m.r. Phenylboronic acid reacts with aldehydes in the presence of a catalytic amount of rhodium(I)–carbene complex, RhCl(COD)(1,3-dialkylbenzimidazolidin-2-ylidene), (2a–f), to give the corresponding aryl secondary alcohols in good yields.
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(a) W.A. Herrmann, L.J. Goossen, C. Köcher and G.R.J. Artus, Angew. Chem. Int. Ed., 35, 2805 (1996); (b) M. Scholl, S. Ding, C.W. Lee and R.H. Grubbs, Org. Lett., 1, 953 (1999); (c) S. Lee, N.A. Beare and J.F. Hartwig, J. Am. Chem. Soc., 123, 8410 (2001); (d) S. Gründemann, M. Albrecht, A. Kovacevic, J.W. Faller and R.H. Crabtree, J. Chem. Soc. Dalton Trans., 2163 (2002); (e) M. Albrecht, R.H. Crabtree, J. Mata and E. Peris, J. Chem. Soc. Chem. Commun., 32 (2002).
B. Cornils W.A. Herrmann (1996) Applied Homogeneous Catalysis with Organometallic Compounds VCH New York
(a) V.P.W. Böhm, C.W.K. Gstottmayr, T. Weskamp and W.A. Herrmann, J. Organomet. Chem., 595, 186 (2000); (b) T. Weskamp, V.P.W. Böhm and W.A. Herrmann, J. Organomet. Chem., 585, 348 (1999).
M.F. Lappert, J.Organomet. Chem., 358, 185 (1988); (b) D. Bourissou, O. Guerret, F.P. Gabbai and G. Bertrand, Chem. Rev., 100, 39 (2000).
(a) D.J. Cardin, M.J. Doyle and M.F. Lappert, J. Chem. Soc. Chem, Commun., 927 (1972); (b) M.J. Doyle, M.F. Lappert, G.M. McLaughlin and J. McMeking, J. Chem. Soc. Dalton Trans., 1495 (1974); (c) D.J. Cardin, B. Çetinkaya, M.F. Lappert, Lj-Manojlovic-muir and K.W. Muir, Chem. Commun., 400 (1971); (d) D.J. Cardin, B. Çetinkaya and M.F. Lappert, Chem. Rev., 72, 545 (1972).
(a) A.J. Arduengo III, H.V.R. Dias, R.L. Harlow and M. Kline, J. Am. Chem. Soc., 114, 5530 (1992); (b) W.A. Herrmann, M. Elison, J. Fischer, C. Köcher and G.R.J. Artus, Chem. Eur. J., 2, 773 (1996).
(a) C. Köcher and W.A. Herrmann, J. Organomet. Chem., 532, 261 (1997); (b) E. Peris, J. A. Loch, J. Mata and R.H. Crabtree, J. Chem. Soc. Chem. Commun., 201 (2001).
(a) V.P.W. Böhm, T. Weskamp, C.W.K. Gstöttmayr and W.A. Herrmann, Angew. Chem. Int. Ed., 39, 1602 (2000); (b) W.A. Herrmann, Angew. Chem. Int. Ed., 4, 1290 (2002).
(a) C.W. Bielawski and R.H. Grubbs, Angew. Chem. Int. Ed., 39, 2903 (2000); (b) A.K. Chatterjee, J.P. Morgan, M. Scholl and R.H. Grubbs, J. Am. Chem. Soc., 122, 3783 (2000).
W.A. Herrmann J.A. Kulpe W. Konkol H. Bahrmann (1990) J. Organomet. Chem. 389 85
(a) M.F. Lappert and R.K. Maskell, J. Organomet. Chem., 264, 217 (1984).
M.G. Gardiner, W.A. Herrmann, C.-P. Reisinger, J. Schwarz and M.J. Spiegler, 572, 239 (1999).
(a) B. Çetinkaya, İ. Özdemir, C. Bruneau and P.H. Dixneuf, J. Mol. Catal. A., 118, L1 (1997); (b) B. Çetinkaya, N. Gürbüz, T. Seçkin and I. Özdemir, J. Mol. Catal. A., 184, 31, (2002).
B. Çetinkaya Ý. Özdemir P.H. Dixneuf (1997) J. Organomet Chem. 534 153
İ. Özdemir S. Demir B. Çetinkaya (2004) J. Mol. Catal. A. 215 45
(a) N. Gürbüz, İ. Özdemir, S. Demir and B. Çetinkaya, J. Mol. Catal. A., 209, 23 (2004); (b) N.Gürbüz, İ. Özdemir, T. Seçkin and B. Çetinkaya, J. Inorg. Organomet. Polym., 14, 149 (2003); (c) İ. Özdemir, B. Çetinkaya, S. Demir and N. Gürbüz, Catalysis. Lett., 97, 37 (2004); (d) İ. Özdemir, B. Alýcý, N. Gürbüz, E. Çetinkaya and B. Çetinkaya, J. Mol. Catal. A., 217, 37 (2004).
(a) B. Çetinkaya, S. Demir, I. Özdemir, L. Toupet, D. Sémeril, C. Bruneau and P.H. Dixneuf, New J. Chem., 25, 519 (2001); (b) B. Çetinkaya, S. Demir, I. Özdemir, L. Toupet, D. Sémeril, C. Bruneau and P.H. Dixneuf, Chem. Eur. J., 9, 2323 (2003).
J.E. Hill T.A. Nile (1997) J. Organomet. Chem. 137 293
A.C. Chen L. Ren A. Decken C.M. Crudden (2000) Organometallics 19 3459
M. Sakai M. Ueda N. Miyaura (1998) Angew. Chem. Int. Ed. 37 3279
A. Fürstner H. Krause (2001) Adv. Synth. Catal. 343 343
J. Chatt and L.M. Venanzi, J. Chem. Soc., 4735 (1975).
(a) O.A. Tarasova, E.Yu. Shmidt, L.V Baikalova, A.I. Mikhaleva and B.A. Trofimov, Izv. Ross. Akad. Nauk. Se. Khim., 11, 2005 (1997); (b) M.R. Haque and M. Rasmussen, Tetrahedron,50, 5535 (1994); (c) E. Çetinkaya, P.B. Hitchcock, H.A. Jasim, M.F. Lappert and K. Spyropoulos, J. Chem. Soc. Perkin Trans., 1, 561 (1992).
B. Çetinkaya P.B. Hitchcock M.F. Lappert D.B. Shaw K. Spyropoulos N.J.W. Warhurst (1993) J. Organomet. Chem. 459 311
I. Özdemir B. Yiğit B. Çetinkaya D. Ülkü M.N. Tahir C. Arici (2001) J. Organomet. Chem. 633 27
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Özdemir, I., Gürbüz, N., Gök, Y. et al. Rhodium-benzimidazolidin-2-ylidene catalyzed addition of arylboronic acids to aldehydes. Transition Met Chem 30, 367–371 (2005). https://doi.org/10.1007/s11243-004-6964-5
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DOI: https://doi.org/10.1007/s11243-004-6964-5