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Issue 8, 2019
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Using para hydrogen induced polarization to study steps in the hydroformylation reaction

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Abstract

A range of iridium complexes, Ir(η3-C3H5)(CO)(PR2R′)2 (1a–1e) [where 1a, PR2R′ = PPh3, 1b P(p-tol)3, 1c PMePh2, 1d PMe2Ph and 1e PMe3] were synthesized and their reactivity as stoichiometric hydroformylation precursors studied. Para-hydrogen assisted NMR spectroscopy detected the following intermediates: Ir(H)23-C3H5)(CO)(PR2R′) (2a–e), Ir(H)21-C3H5)(CO)(PR2R′)2 (4d–e), Ir(H)21-C3H5)(CO)2(PR2R′) (10a–e), Ir(H)2(CO–C3H5)(CO)2(PR2R′) (11a–c), Ir(H)2(CO–C3H7)(CO)2(PR2R′) (12a–c) and Ir(H)2(CO–C3H5)(CO)(PR2R′)2 (13d–e). Some of these species exist as two geometric isomers according to their multinuclear NMR characteristics. The NMR studies suggest a role for the following 16 electron species in these reactions: Ir(η3-C3H5)(CO)(PR2R′), Ir(η1-C3H5)(CO)(PR2R′)2, Ir(η1-C3H5)(CO)2(PR2R′), Ir(CO–C3H5)(CO)2(PR2R′), Ir(CO–C3H7)(CO)2(PR2R′) and Ir(CO–C3H5)(CO)(PR2R′)2. Their role is linked to several 18 electron species in order to confirm the route by which hydroformylation and hydrogenation proceeds.

Graphical abstract: Using para hydrogen induced polarization to study steps in the hydroformylation reaction

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Publication details

The article was received on 29 Nov 2018, accepted on 24 Jan 2019 and first published on 25 Jan 2019


Article type: Paper
DOI: 10.1039/C8DT04723E
Citation: Dalton Trans., 2019,48, 2664-2675

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    Using para hydrogen induced polarization to study steps in the hydroformylation reaction

    D. Guan, C. Godard, S. M. Polas, R. P. Tooze, A. C. Whitwood and S. B. Duckett, Dalton Trans., 2019, 48, 2664
    DOI: 10.1039/C8DT04723E

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