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Following palladium catalyzed methoxycarbonylation by hyperpolarized NMR spectroscopy: a parahydrogen based investigation

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Abstract

Pd(OTf)2(bcope) is shown to react in methanol solution with diphenylacetylene, carbon monoxide and hydrogen to produce the methoxy-carbonylation product methyl 2,3 diphenyl acrylate alongside cis- and trans-stilbene. In situ NMR studies harnessing the parahydrogen induced polarization effect reveal substantially enhanced 1H NMR signals in both protic and aprotic solvents for a series of reaction intermediates that play a direct role in this homogeneous transformation. Exchange spectroscopy (EXSY) measurements reveal that the corresponding CO adducts are less reactive than their methanol counterparts.

Graphical abstract: Following palladium catalyzed methoxycarbonylation by hyperpolarized NMR spectroscopy: a parahydrogen based investigation

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Publication details

The article was received on 10 Feb 2017, accepted on 20 Apr 2017 and first published on 21 Apr 2017


Article type: Paper
DOI: 10.1039/C7CY00252A
Citation: Catal. Sci. Technol., 2017, Advance Article
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    Following palladium catalyzed methoxycarbonylation by hyperpolarized NMR spectroscopy: a parahydrogen based investigation

    D. Guan, A. Jonathan Holmes, J. López-Serrano and S. B. Duckett, Catal. Sci. Technol., 2017, Advance Article , DOI: 10.1039/C7CY00252A

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