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Journal of the American Chemical Society
BisꢀAlkoxycarbonylation of Olefins for the Synthesis of Substituted Succinic
Corresponding Author
Diesters. Adv. Synth. Catal. 2015, 357, 177ꢀ184; For selected chiral examples,
see: (g) Pisano, C.; Nefkens, S. C. A.; Consiglio, G. Stereochemistry of the
dicarbonylation of olefins using styrene as the model compound. Organometal-
lics 1992, 11, 1975ꢀ1978; (h) Nefkens, S. C. A.; Sperrle, M.; Consiglio, G.
PalladiumꢀCatalyzed Enantioselective Bisꢀalkoxycarbonylation of Olefins.
Angew. Chem. Int. Ed. Engl. 1993, 32, 1719ꢀ1720; (i) Wang, L.; Kwok, W.; Wu,
J.; Guo, R.; AuꢀYeung, T. T. L.; Zhou, Z.; Chan, A. S. C.; Chan, K. S. Enantioseꢀ
lective bisꢀalkoxycarbonylation of styrene catalyzed by novel chiral dipyriꢀ
dylphosphine cationic palladium(II) complexesOriginal. J. Mol. Catal. A. 2003,
196, 171ꢀ178; (j) Gao, Y.ꢀX.; Chang, L.; Shi, H.; Liang, B.; Wongkhan, K.;
Chaiyaveij, D.; Batsanov, A. S.; Marder, T. B.; Li, C.ꢀC.; Yang, Z.; Huang, Y. A
ThioureaꢀOxazoline Library with Axial Chirality: Ligand Synthesis and Studies
of the PalladiumꢀCatalyzed Enantioselective Bis(methoxycarbonylation) of
Terminal Olefins. Adv. Synth. Catal. 2010, 352, 1955ꢀ1966.
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Author Contributions
The manuscript was written through contributions of all authors. / All
authors have given approval to the final version of the manuscript. /
Notes
The authors declare no competing financial interest.
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ACKNOWLEDGMENT
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This work is supported by Evonik Performance Materials GmbH and
the State of MecklenburgꢀVorpommern. We thank the analytical team
of LIKAT for their kind support.
[5] Inoue, S.; Yokota, K.; Tatamidani, H.; Fukumoto, Y.; Chatani, N. Chelationꢀ
Assisted Transformation:ꢀ Synthesis of 1,4ꢀDicarboxylate Esters by the Rhꢀ
Catalyzed Carbonylation of Internal Alkynes with Pyridinꢀ2ꢀylmethanol Org.
Lett. 2006, 8, 2519ꢀ2522.
ABBREVIATIONS
PTSA.H2O, pꢀtoluenesulfonic acid monohydrate; Py, Pyridine.
[6] Ali, B. E.; Alper, H. Synthesis of unsaturated esters, including tꢀalkyl esters,
by the palladiumꢀcatalyzed carbonylation of alkynes in the presence of alcohols
and 1,4ꢀbis(diphenylphosphino)butane. J. Mol. Catal. 1991, 67, 29ꢀ33.
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