Communication
.6 M H SO , 1.5 ml acetic acid, 40 bar CO, 80 °C, and 20 h).
As shown in Scheme 2, the palladium catalyst formed all
expected C-9 acids, while in the presence of the platinum
system only 1-octene is carbonylated.
Catalysis Science & Technology
0
Damian, H. van Rensburg, A. M. Z. Slawin, R. P. Tooze and
M. L. Clarke, Chem. – Eur. J., 2009, 15, 10504–10513; J. A.
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4 P. Roesle, C. J. Dürr, H. M. Möller, L. Cavallo, L. Caporaso
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2
4
Finally, hydroxycarbonylation reactions of 1-butene,
2
-butene, and iso-butene, which resemble the main
constituents of the industrially produced and used olefin
mixture raffinate 1 were explored. Measuring the pressure
consumption during the reactions revealed again that
platinum prefers hydroxycarbonylation of the terminal
unbranched olefin (1-butene), while no reaction occurred
with iso-butene Fig. 1).
Conclusions
T. Xu, F. Sha and H. Alper, J. Am. Chem. Soc., 2016, 138,
5
In conclusion, we report the first protocol for a platinum-
catalysed hydroxycarbonylation of olefins. Specifically the
6
2
629–6635; H. Liu, N. Yan and P. J. Dyson, Chem. Commun.,
014, 50, 7848–7851; G. Zhang, B. Gao and H. Huang, Angew.
combination
of
2
PtCl /2,2′-bis(tert-butyl(pyridin-2-yl)
Chem., Int. Ed., 2015, 54, 7657–7661; J. Liu, H. Li, A.
Spannenberg, R. Franke, R. Jackstell and M. Beller, Angew.
Chem., Int. Ed., 2016, 55, 13544–13548.
A. A. Núñez Magro, L. M. Robb, P. J. Pogorzelec, A. M. Z.
Slawin, G. R. Eastham and D. J. Cole-Hamilton, Chem. Sci.,
phosphanyl)-1,1′-binaphthalene (Neolephos) allowed for
selective carbonylation of aliphatic olefins to the corresponding
carboxylic acids. Compared to related palladium complexes,
the work here presented a catalyst system which selectively
addresses terminal unbranched aliphatic olefins, which can be
useful for process intensification applications.
6
2
010, 1, 723–730; Y. Katafuchi, T. Fujihara, T. Iwai, J. Terao
and Y. Tsuji, Adv. Synth. Catal., 2011, 353, 475–482; R.
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Conflicts of interest
2
010, 24, 38–46; D. B. G. Williams, M. L. Shaw and T.
Hughes, Organometallics, 2011, 30, 4968–4973; M. Schmidt,
C. Urban, S. Schmidt and R. Schomäcker, ACS Omega,
There are no conflicts to declare.
2
018, 3, 13355–13364.
Acknowledgements
7
8
9
K. Dong, R. Sang, J. Liu, R. Razzaq, R. Franke, R. Jackstell
and M. Beller, Angew. Chem., Int. Ed., 2017, 56, 6203–6207.
C. Schneider, R. Jackstell, B. U. W. Maes and M. Beller, Eur.
J. Org. Chem., 2020, 8, 932–936.
F. E. Paulik and J. F. Roth, Chem. Commun., 1968, 1578a;
C. M. Thomas and G. Süss-Fink, Coord. Chem. Rev.,
This work has been funded by the Evonik Industries, the
German Federal Ministry BMBF and the State of
Mecklenburg-Western Pommerania.
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