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17 results on '"de Gelder, René"'

1. The Crystalline Sponge Method in Water

Author

de Poel, Wester, primary, Tinnemans, Paul, additional, Duchateau, Alexander L. L., additional, Honing, Maarten, additional, Rutjes, Floris P. J. T., additional, Vlieg, Elias, additional, and de Gelder, René, additional

Published
2019
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5. Formal Synthesis of Solanoeclepin A: Enantioselective Allene Diboration and Intramolecular [2+2] Photocycloaddition for the Construction of the Tricyclic Core.

Author

Kleinnijenhuis, Roel A., Timmer, Brian J. J., Lutteke, Ginger, Smits, Jan M. M., de Gelder, René, van Maarseveen, Jan H., and Hiemstra, Henk

Subjects
ALLENE crystals, DIOLEFINS, PHOTOCYCLOADDITION, RING formation (Chemistry), ALLENE
Abstract

An enantioselective synthesis of an intermediate in the Tanino total synthesis of solanoeclepin A has been developed. The key step was an intramolecular [2+2] photocycloaddition, which led to the tricyclo[5.2.1.01, 6]decane core in six steps. The first photosubstrate, prepared through an indium-mediated Barbier-type reaction, gave an excellent [2+2] cycloaddition, but it could not be obtained in sufficient enantiopurity. The second photosubstrate, prepared through an asymmetric allene diborylation in high enantiomeric excess, gave the [2+2] cycloaddition product in high yield on irradiation at 365 nm on 20 g scale in a flow system. Other important steps were the replacement of a boronate group at the quaternary carbon by a vinyl group and diastereoselective cyclopropanation of an allylic alcohol. [ABSTRACT FROM AUTHOR]

Published
2016
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10. Selective Oxidation of [RhI(cod)]+ by H2O2 and O2

Author

de Bruin, Bas, primary, Boerakker, M. J., additional, Brands, Johanna A., additional, Donners, Jack J. J. M., additional, Donners, Maurice P. J., additional, de Gelder, René, additional, Smits, Jan M. M., additional, Gal, Anton W., additional, and Spek, Anton L., additional

Published
1999
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15. Steric Control over Arene Coordination to β‐Diiminate Rhodium(I) Fragments

Author

Budzelaar, Peter H. M., Moonen, Nicolle N. P., de Gelder, René, Smits, Jan M. M., and Gal, Anton W.

Abstract

The bulky ligands Lx−(Lx=(2, 6‐C6H3X2)NC(Me)CHC(Me)N(2, 6‐C6H3X2), X=Cl, Me) can be used to generate fluxional mononuclear arene complexes [LXRh(η4‐arene)] (arene=benzene, toluene, m‐xylene, mesitylene), which for X=Me disproportionate to fluxional dinuclear complexes [{LMeRh}2(anti‐μ‐arene)]. For both mononuclear and dinuclear complexes, steric interactions do not stop the fluxionality but govern the preferred orientation of the methyl‐substituted arenes, thus allowing indirect determination of the static NMR parameters. For the μ‐arene complexes, two distinct types of fluxionality are proposed on the basis of calculations: ring rotation and metal shift. In the solid state, the toluene complex has an η4(1,2,3,4):η4(3,4,5,6)‐bridged structure; the NMR analysis indicates that the benzene and m‐xylene complexes have similar structures. The mesitylene complex, however, has an unprecedented η3(1,2,3):η3(3,4,5)‐bridged structure, which is proposed to correspond to the transition state for arene rotation in the other cases. Steric factors are thought to be responsible for this reversal of stabilities.

Published
2000
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16. 2‐Rhodaoxetanes: Their Formation of Oxidation of [RhI(ethene)]+and Their Reactivity upon Protonation

Author

de Bruin, Bas, Boerakker, Mark J., Verhagen, Johanna A. W., de Gelder, René, Smits, Jan M. M., and Gal, Anton W.

Abstract

The selective oxidation of [(N4)RhI(ethene)]+(N4= tetradentate N ligand)results in stable 2‐rhodaoxetanes (RhIII‐κ2‐C,O‐2‐oxyethyl complexes) that become reactive upon protonation of the 2‐rhodaoxetane oxygen atom (see scheme). Metallaoxetane rearrangement changes from the elimination of acetaldehyde in a non‐coordinating solvent to the formation of a metallacyclic amide in acetonitrile. The observed stoichiometric amidation of coordinated ethene might indicate new possibilities for catalytic formation of C‐N bonds.

Published
2000
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17. Selective Oxidation of [RhI(cod)]+by H2O2and O2

Author

de Bruin, Bas, Boerakker, M. J., Brands, Johanna A., Donners, Jack J. J. M., Donners, Maurice P. J., de Gelder, René, Smits, Jan M. M., Gal, Anton W., and Spek, Anton L.

Abstract

2‐Rhodaoxetanes have thus far not been invokedas intermediates in rhodium‐catalysed oxidation of olefins. Oxygenation of one COD double bond in cationic complexes [′N3′RhI(cod)]+by H2O2and O2is now found to result in 2‐rhodaoxetanes that subsequently rearrange (see figure). Insight into their modes of formation and rearrangement might contribute to a better understanding of late transition metal catalysed oxidation of olefins.

Published
1999
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