By I Fairlamb; Jason M LyNAm
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R. Powell, J. Am. Chem. , 1997, 119, 11817. 72 C. P. Casey, E. L. Paulsen, E. W. Beuttenmueller, B. R. Proft, B. A. Matter and D. R. Powell, J. Am. Chem. , 1999, 121, 63. 73 L. A. van der Veen, M. d. K. Boele, F. R. Bregman, P. C. J. Kamer, P. W. van Leeuwen, K. Gobitz, J. Fraanje, H. Schenk and C. Bo, J. Am. Chem. , 1998, 120, 11616. Organomet. 1039/B801377M View Online 74 C. F. Hobbs and W. S. Knowles, J. Org. , 1981, 46, 4422. 75 U. Nettekoven, P. C. J. Kamer, M. Widhalm and P. W. N. M. van Leeuwen, Organometallics, 2000, 19, 4596.
Higher selectivity for the linear aldehyde when both electron poor phosphines are both in the equatorial position (Fig. 10). Further investigations using electronically dissymmetric DIPHOS derivatives (Fig. 11) have shown that the diphosphine will tend to coordinate Fig. 10 Coordination modes of ligands in iridium complexes and the selectivity ratios achieved in the Rh-catalysed hydroformylation of hex-1-ene. 38 | Organomet. 1039/B801377M View Online Fig. 11 Non-symmetric electron deﬁcient diphos analogues give improved regioselectivity in hydroformylation of hex-1-ene.
Further studies are clearly warranted in order to detail the working mode of the catalyst. Activation of dihydrogen with complex 30 may occur either prior to, or after oleﬁn coordination to the palladium centre. According to the reactivity patterns described above, oxidative H2 addition to the palladium centre seems most likely to occur. Subsequent reductive elimination of the carbene ligand as imidazolium cation residue would be analogous to the process described in Scheme 3. The use of chelating dicarbene ligands is expected to hamper such reductive elimination sequences or at least shift an eventual equilibrium to the cyclometallated side, though perhaps, insuﬃciently.