Abstract
Our interest in palladium-catalyzed olefin carbonylation was awakened by the discovery of a class of highly efficient cationic palladium catalysts for the alternating copolymerization of olefins with carbon monoxide (Equation 1) [1].
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Drent, E.; Eur. Patent Appl. EP 121,965, 1984 (to Shell).
(a) Drent, E.; van Broekhoven, J. A. M.; Doyle, M. J. J. Organomet. Chem. 1991, 417, 235. (b) Sen, A. Ace. Chem. Res. 1993, 26, 303. (c) Budzelaar, P. H. M.; Drent, E. Chem. Rev. 1996, 96, 663.
Roelen, O. Deutsches Patent Schrift 849,548, 1938/1952, US Pat. 2,327,066, 1943, Chem. Exp. Didakt, 119, 3, 1977.
(a) Cornils, B. in New Syntheses with Carbon Monoxide; Falbe, J., Ed.; Springer-Verlag: Heidelberg, 1980. (b) For a review on the production of low molecular weight oxygenates from CO and ethene, see Robertson, R. A. M.; Cole-Hamilton, D. J. Coord. Chem. Rev. 2002, 225, 67.
(a) Drent, E. Eur. Pat. Appl. EP 220,767, 1985. (b) Drent, E. UK Pat. Appl. 2,183,631, 1985.
‘Reppe’ carbonylation, the reaction of an unsaturated hydrocarbon substrate, a carbonyl source and a nucleophile has been recently reviewed: Kiss, G. Chem. Rev 2001, 101, 3435.
Drent, E.; Kragtwijk, E. Eur. Pat. Appl. EP 495, 548, 1992 (to Shell).
(a) Eastham, G. R.; Tooze, R. P.; Wang, X. L.; Whiston, K. World Pat., 96/19434, 1996 (to ICI), (b) Clegg, W.; Eastham, G. R.; Elsegood, M. R. J.; Tooze, R. P.; Wang, X. L.; Whiston, K. Chem.Commun. 1999, 1877.
(a) Eastham, G. R.; Heaton, B. T.; Iggo, J. A.; Tooze, R. P.; Whyman, R.; Zacchini, S. Chem. Commun. 2000, 609. (b) Clegg, W.; Eastham, G. R.; Elsegood, M. R. J.; Heaton, B. T.; Iggo, J. A.; Tooze, R. P.; Whyman, R.; Zacchini, S. Organometallics, 2002, 21, 1832. (c) The two-cycle (Pd-H and Pd-alkoxy) mechanism for polyketone formation implies that any polyketone catalyst for which the terminating alcoholysis of Pd-acyl is fast relative to chain propagation will automatically end-up in the Pd-H cycle for methyl propionate formation, even if the very first cycle would start at Pd-methoxide (generating one molecule of succinate)
Reman, W. G.; de Boer, G. B. J; van Langen, S. A. J.; Nahuijsen, A. Eur. Pat. Appl. EP 411, 721, 1989 (to Shell).
Tooze, R. P.; Whiston, K.; Malyan, A. P.; Taylor, M. J.; Wilson, N. W. J. Chem Soc, Dalton Trans. 2000, 3441.
Drent, E.; Pugh, R. I. Adv. Synth. Catal., manuscript in preparation.
Zuideveld, M. A.; Kamer, P. C. J.; van Leeuwen, P.W.N.M.; Klusener, P. A. A; Stil, H.A; Roobeek, C. F. J. Am. Chem. Soc. 1998, 120, 7977.
(a) Mulders, J.P. Neth. Pat. 6604094, 1966 (to Shell), (b) Mason, R. F.; Winkle, J. L. V. US Pat. 3,400,163, 1968 (to Shell).
(a) Drent, E.; Kragtwijk, E.; Pello, D. H. L.; Eur. Pat. Appl. EP 495,547 A2, 1992 (to Shell), (b) Drent, E.; Pello, D. H. L.; Suykerbuyk, J. C. J. L.; van Gogh, J. B. World. Pat., 5354, 1994 (to Shell) (c) Eberhard, M. R. Ph. D. thesis, University of Bristol, 2001.
Drent, E.; Jager, W. W. unpublished results.
(a) Epstein, M.; Buckler, S. A. J. Am. Chem. Soc. 1961, 83, 3279. (b) Epstein, M.; Buckler, S.A. US Pat. 3,050,531, 1962 (to American Cyanamid Co.).
(a) Drent, E.; Pringle, P. G.; Suykerbuyk, J. C. L. J. World. Pat. W098/42717, 1998 (to Shell), (b) Gee, V.; Open, A. G.; Phetmung, H.; Pringle, P. G.; Pugh, R. I. Chem. Commun. 1999, 901.
(a) Drent, E.; Pringle, P. G.; Pugh, R. I. World Pat. 01/28972, 2001 (to Shell), (b) Pugh, R. I.; Pringle, P. G.; Drent, E. Chem. Commun. 2001, 1476.
Ahlers, W. World Pat. 01/85661, 2001 (to BASF).
Drent, E.; Keijsper, J. J. Eur. Pat. Appl. 522, 635, 1993 (to Shell).
Budzelaar, P.H.M.; Drent, E. J. Organomet. Chem. 2000, 593–594, 211.
Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen; P. W. N. M.; Roobeek, C. F. J. Organomet. Chem. 1992, 430, 357.
Tolman, C. A. Chem. Rev 1977, 77, 313.
(a) Rix, F. C; Brookhart, M.; White, P. S. J. Am. Chem. Soc. 1996, 118, 4746. (b) Margl, P.; Ziegler, T. Organometallics, 1996, 15, 5519.
Drent, E.; Pello, D. H. L.; Suykerbuyk, J. C. L. J.; Van Gogh, J. World. Pat. WO 9505354, 1995 (to Shell).
Comils, B. in New syntheses with carbon monoxide; Falbe, J., Ed.; Springer-Verlag: Heidelberg, 1980, p. 162.
van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. H. N.; Dierkes, P. Chem. Rev. 2000, 100, 2741.
For representative examples, see: (a) van der Veen, L. A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Angew. Chem., Int. Ed. 1999, 38, 336. (b) Klein, H.; Jackstell, R.; Wiese, K.D.; Borgmann, C; Belier, M. Angew. Chem., Int. Ed 2001, 40, 3408.
For example, see: Selent, D.; Hess, D.; Wiese, K. D.; Rottger, D.; Kunze, C; Borner, A. Angew. Chem., Int. Ed. 2001, 40, 1696.
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Pugh, R.I., Drent, E. (2003). Palladium-Catalysed Synthesis of Mono-Esters, -Ketones and — Aldehydes/Alcohols. In: Sen, A. (eds) Catalytic Synthesis of Alkene-Carbon Monoxide Copolymers and Cooligomers. Catalysis by Metal Complexes, vol 27. Springer, Boston, MA. https://doi.org/10.1007/978-1-4419-9266-6_2
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