Abstract
A first effort employing a range of polar-group functionalized phosphines (L 1 –L 7 ) to design mononuclear Rh(I) compounds of [Rh(quin-8-O)(CO)(L)] (quin-8-O = 8-hydroxy quinolate) is described. The reaction of a Rh(I) precursor [Rh(μ-Cl)(CO)2]2 with 8-hydroxyquinoline in the presence of a base followed by phosphines (L 1 –L 7 ) produced only a single isomer of [Rh(quin-8-O)(CO)(L)] compounds (1–7) with pendant, i.e. non-bonded, polar-groups (includes carboxyl, hydroxyl and formyl). A relationship between Δgd31P chemical shifts and the ν(C≡O) was derived to evaluate and explain the σ-donor properties of these phosphines with respect to the electronic properties of the polar groups and the extent of π-back-bonding to the CO group. These mononuclear Rh(I)-Phosphines were investigated as catalysts in the hydroformylation of 1-hexene and cyclohexene in aqueous two-phase and single-phase solvent systems. The Rh(I) catalysts with strong σ-donor and hydrophilic phosphines provided better yields and selectivities for the hydroformylation products, which is a reverse trend compared to literature reports. When the Rh(I) compounds contained strong σ-donor phosphines, the π-acceptor properties of the pyridine ring of 8-hydroxyquinolate were found to be beneficial for the facile cleavage of the CO group during hydroformylation, and additionally, to improve the kinetic stability of catalysts. 
[1] A.M. Dreis, C.J. Douglas, J. Am. Chem. Soc. 131, 412 (2009) http://dx.doi.org/10.1021/ja806630810.1021/ja8066308Search in Google Scholar
[2] C.N. Garon et al., Dalton Trans. 1624 (2009) 10.1039/b812259hSearch in Google Scholar
[3] V.R. Landaeta, F. López-Linares, R. Sánchez-Delgado, C. Bianchini, F. Zanobini, M. Peruzzini, J. Mol. Cat. A 301, 1 (2009) http://dx.doi.org/10.1016/j.molcata.2008.11.01310.1016/j.molcata.2008.11.013Search in Google Scholar
[4] E.G. Kuntz, Chemtech. 17, 570 (1987) 10.1016/S0190-9622(87)80442-5Search in Google Scholar
[5] B. Cornills, E.G. Kuntz, J. Organomet. Chem. 502, 177 (1995) http://dx.doi.org/10.1016/0022-328X(95)05820-F10.1016/0022-328X(95)05820-FSearch in Google Scholar
[6] E.G. Kuntz, French Patent 2 314 910 (1975) Search in Google Scholar
[7] W.A. Herrmann, C.W. Kohlpaintner, Inorg. Synth. 32, 8 (1998) http://dx.doi.org/10.1002/9780470132630.ch210.1002/9780470132630.ch2Search in Google Scholar
[8] H. Fu et al., J. Mol. Cat. A 292, 21 (2008) http://dx.doi.org/10.1016/j.molcata.2008.06.00510.1016/j.molcata.2008.06.005Search in Google Scholar
[9] S. Tilloy, G. Crowyn, E. Monflier, P.W.N.M. van Leeuwen, J.N.H. Reek, New J. Chem. 377 (2006) 10.1039/b515364fSearch in Google Scholar
[10] D. Baskakov, W.A. Herrmann, J. Mol. Cat. A 283, 166 (2008) http://dx.doi.org/10.1016/j.molcata.2007.12.00610.1016/j.molcata.2007.12.006Search in Google Scholar
[11] D.J. Adams et al., Dalton Trans. 3862 (2005) 10.1039/b510766kSearch in Google Scholar PubMed
[12] Q. Lin, W. Jiang, H. Fu, H. Chen, X. Li, Applied Cat. A 328, 83 (2007) http://dx.doi.org/10.1016/j.apcata.2007.05.03210.1016/j.apcata.2007.05.032Search in Google Scholar
[13] P.J. Baricelli et al., J. Mol. Cat. A 278, 107 (2007) http://dx.doi.org/10.1016/j.molcata.2007.07.02510.1016/j.molcata.2007.07.025Search in Google Scholar
[14] D. Baskakov, W.A. Herrmann, J. Mol. Cat. A 283, 166 (2008) http://dx.doi.org/10.1016/j.molcata.2007.12.00610.1016/j.molcata.2007.12.006Search in Google Scholar
[15] P.J. Baricelli et al., J. Mol. Cat. A, 291, 12 (2008). http://dx.doi.org/10.1016/j.molcata.2008.05.01010.1016/j.molcata.2008.05.010Search in Google Scholar
[16] P. Kalck, Pure & Appl. Chem. 61, 967 (1989) http://dx.doi.org/10.1351/pac19896105096710.1351/pac198961050967Search in Google Scholar
[17] P.J. Baricelli, F. Lopez-Linares, A. Bruss, R. Santos, E. Lujano, R.A. Sanchez-Delgado, J. Mol. Cat. A 239, 130 (2005) http://dx.doi.org/10.1016/j.molcata.2005.06.00610.1016/j.molcata.2005.06.006Search in Google Scholar
[18] K.H. Shaughnessy, Chem. Rev. 109, 643 (2009) http://dx.doi.org/10.1021/cr800403r10.1021/cr800403rSearch in Google Scholar
[19] N. Pinault, D.W. Bruce, Coord. Chem. Rev. 241, 1 (2003) http://dx.doi.org/10.1016/S0010-8545(02)00306-510.1016/S0010-8545(02)00306-5Search in Google Scholar
[20] K. Ahlford, J. Lind, L. Maler, H. Adolfsson, Green Chem. 832 (2008) 10.1039/b806177gSearch in Google Scholar
[21] C. Jimenez-Rodriguez, P.J. Pogorzelec, G.R. Eastham, A.M.Z. Slawin, D.J. Cole-Hamilton, Dalton Trans. 4160 (2007) 10.1039/b701582hSearch in Google Scholar
[22] S. Liu, J. Xiao, J. Mol. Cat. A 270, 1 (2007) http://dx.doi.org/10.1016/j.molcata.2007.01.00310.1016/j.molcata.2007.01.003Search in Google Scholar
[23] Y.S. Varshavsky, M.R. Galding, T.G. Cherkasova, S.N. Smirnov, V.N. Khrustalev, J. Organomet. Chem. 692, 5788 (2007) http://dx.doi.org/10.1016/j.jorganchem.2007.09.02210.1016/j.jorganchem.2007.09.022Search in Google Scholar
[24] M.M. Conradie, J. Conradie, Inorg. Chim. Acta 362, 519 (2009) http://dx.doi.org/10.1016/j.ica.2008.04.04610.1016/j.ica.2008.04.046Search in Google Scholar
[25] G. Franciò, D. Drommi, C. Graiff, F. Faraone, A. Tiripicchio, Inorg. Chim. Acta 338, 14 (2002) http://dx.doi.org/10.1016/S0020-1693(02)00849-610.1016/S0020-1693(02)00849-6Search in Google Scholar
[26] E. Mieczynska, A. Trzeciak, R. Grzybek, J.J. Ziolkowski, J. Mol. Cat. A. 132, 203 (1998) http://dx.doi.org/10.1016/S1381-1169(97)00244-610.1016/S1381-1169(97)00244-6Search in Google Scholar
[27] G. Steyl, Polyhedron 26, 5324 (2007) http://dx.doi.org/10.1016/j.poly.2007.07.03910.1016/j.poly.2007.07.039Search in Google Scholar
[28] X.Y. Huang, R.X. Li, H. Chen, X.J. Li, Chinese Chem. Lett. 14, 623 (2003) Search in Google Scholar
[29] F. Kwaskowska-Chec, A.M. Trzeciak, Transition Met. Chem. 16, 212 (1991) http://dx.doi.org/10.1007/BF0103283710.1007/BF01032837Search in Google Scholar
[30] J. Zhang, X.Z. Sun, M. Poliakoff, M.W. George, J. Organomet. Chem. 678, 128 (2003) http://dx.doi.org/10.1016/S0022-328X(03)00439-X10.1016/S0022-328X(03)00439-XSearch in Google Scholar
[31] W. Simanko, K. Mereiter, R. Schmid, K. Kirchner, A.M. Trzeciak, J.J. Ziokowski, J. Organomet. Chem. 602, 59 (2000) http://dx.doi.org/10.1016/S0022-328X(00)00118-210.1016/S0022-328X(00)00118-2Search in Google Scholar
[32] A. Brink, A. Roodt, H.G. Visser, Acta Cryst. E63, m48 (2007) 10.1107/S160053680604966XSearch in Google Scholar
[33] J.M. Janse van Rensburg, A. Muller, A. Roodt, Acta Cryst. E63, m3015 (2007) 10.1107/S1600536807056152Search in Google Scholar
[34] J.M. Janse van Rensburg, A. Roodt, A. Muller, Acta Cryst. E62, m1040 (2006) 10.1107/S1600536806012955Search in Google Scholar
[35] V. Ravinder, H. Shumann, J. Blum, Synth. Commun. 22, 841 (1992) http://dx.doi.org/10.1080/0039791920802084810.1080/00397919208020848Search in Google Scholar
[36] V. Ravinder, H. Shumann, J. Blum, Synth. Commun. 22, 1453 (1992) http://dx.doi.org/10.1080/0039791920802161310.1080/00397919208021613Search in Google Scholar
[37] H. Schumann, V. Ravinder, L. Meltser, W. Baidossi, Y. Sasson, J. Blum, J. Mol. Cat. A 118, 55 (1997) http://dx.doi.org/10.1016/S1381-1169(96)00374-310.1016/S1381-1169(96)00374-3Search in Google Scholar
[38] H. Schumann, H. HemLing, V. Ravinder, Y. Badrieh, J. Blum, J. Organomet. Chem. 469, 213 (1994) http://dx.doi.org/10.1016/0022-328X(94)88075-110.1016/0022-328X(94)88075-1Search in Google Scholar
[39] J.M. Janse van Rensburg, A. Roodt, A. Muller, R. Meijboom, Acta Cryst. E61, m1741 (2005) 10.1107/S1600536805024967Search in Google Scholar
[40] M.M. Amini, M.M. Farnaze Yaganeh, H.R. Khavasi, P. Mirzaei, S.W. Ng, Transition Met. Chem. 33, 79 (2008) http://dx.doi.org/10.1007/s11243-007-9017-z10.1007/s11243-007-9017-zSearch in Google Scholar
[41] F. Artizzu et al., Inorg. Chem. 44, 2005 (2005) http://dx.doi.org/10.1021/ic048389510.1021/ic0483895Search in Google Scholar PubMed
[42] N. Vijayan et al., Cryst. Res. Technol. 42, 195 (2007) http://dx.doi.org/10.1002/crat.20061079610.1002/crat.200610796Search in Google Scholar
[43] L.J. Bellamy, The Infrared Spectra of Complex Molecules (Richard Clay and Company, Ltd., Bungay, Suffolk, 1964) 277 Search in Google Scholar
[44] G.M. Bodner, M.P. May, L.E. McKinney, Inorg. Chem. 19, 1951 (1980) http://dx.doi.org/10.1021/ic50209a02510.1021/ic50209a025Search in Google Scholar
[45] G.M. Bodner, Inorg. Chem. 14, 1932 (1975) http://dx.doi.org/10.1021/ic50150a03910.1021/ic50150a039Search in Google Scholar
[46] G.M. Bodner, L.J. Todd, Inorg. Chem. 13, 1335 (1974) http://dx.doi.org/10.1021/ic50136a01710.1021/ic50136a017Search in Google Scholar
[47] G.M. Bodner, S.B. Kahl, K. Bork, B.N. Storhoff, J.E. Wuller, L.J. Todd, Inorg. Chem. 12, 1071 (1973) http://dx.doi.org/10.1021/ic50123a01810.1021/ic50123a018Search in Google Scholar
[48] O. Kuhl, Coord. Chem. Rev. 249, 693 (2005) http://dx.doi.org/10.1016/j.ccr.2004.08.02110.1016/j.ccr.2004.08.021Search in Google Scholar
[49] S. Basu, I. Pal, R.J. Butcher, G. Rosair, S. Bhattacharya, J. Chem. Sci. 117, 167 (2005) 10.1007/BF03356112Search in Google Scholar
[50] P.C.J. Kamer, A. van Rooy, G.C. Schoemaker, P.W.N.M. van Leeuwen, Coord. Chem. Rev. 248, 2409 (2004) http://dx.doi.org/10.1016/j.ccr.2004.06.00610.1016/j.ccr.2004.06.006Search in Google Scholar
[51] W.R. Moser, C.J. Papile, D.A. Brannon, R.A. Duwell, S.J. Weininger, J. Mol. Catal. 41, 271 (1987) http://dx.doi.org/10.1016/0304-5102(87)80106-210.1016/0304-5102(87)80106-2Search in Google Scholar
[52] B. Pitteri, M. Bortoluzzi, Eur. J. Inorg. Chem. 2007, 4456 (2007) http://dx.doi.org/10.1002/ejic.20070045710.1002/ejic.200700457Search in Google Scholar
[53] S.H. Park, M.C. Milletti, N. Gardner, Polyhedron 17, 1267 (1998) http://dx.doi.org/10.1016/S0277-5387(97)00396-310.1016/S0277-5387(97)00396-3Search in Google Scholar
[54] A. Das, S.A. Trammell, M.H. Hecht, Biophy. Chem. 123, 102 (2006) http://dx.doi.org/10.1016/j.bpc.2006.04.01110.1016/j.bpc.2006.04.011Search in Google Scholar
[55] J.Y. Kim, S.M. Park, H. So, Bull. Korean Chem. Soc. 18, 369 (1997) Search in Google Scholar
[56] M.A Kakli, E.G. Delmar, R.C. Tailor, Synt. React. Inorg. Metal-Org. Chem. 5, 357 (1975) http://dx.doi.org/10.1080/0094571750805732810.1080/00945717508057328Search in Google Scholar
[57] D. Noskova, J. Padlahova, Polyhedron 2, 349 (1983) http://dx.doi.org/10.1016/S0277-5387(00)83927-310.1016/S0277-5387(00)83927-3Search in Google Scholar
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