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Journal Article

Molybdenum Nitride Complexes with Ph3SiO Ligands Are Exceedingly Practical and Tolerant Precatalysts for Alkyne Metathesis and Efficient Nitrogen Transfer Agents

MPS-Authors
http://pubman.mpdl.mpg.de/cone/persons/resource/persons58429

Bindl,  Martin
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons59012

Stade,  Robert
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58614

Heilmann,  Eike K.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58887

Picot,  Alexandre
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58578

Goddard,  Richard
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58380

Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Supplementary Material (public)

[262]SI1.pdf
(Supplementary material), 76KB

[262]SI2.pdf
(Supplementary material), 5MB

ja903259g_si_001.cif
(Supplementary material), 35KB

Citation

Bindl, M., Stade, R., Heilmann, E. K., Picot, A., Goddard, R., & Fürstner, A. (2009). Molybdenum Nitride Complexes with Ph3SiO Ligands Are Exceedingly Practical and Tolerant Precatalysts for Alkyne Metathesis and Efficient Nitrogen Transfer Agents. Journal of the American Chemical Society, 131(27), 9468-9470. doi:10.1021/ja903259g.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-8EA1-E
Abstract
The molybdenum nitride complex [(Ph3SiO)3Mo≡N] (10), which can be conveniently prepared in situ from readily available [(Me3SiO)2((Me3Si)2N)Mo≡N] (9) and Ph3SiOH, and the pyridine adduct of 10, [(pyridine)(Ph3SiO)3Mo≡N] (11), exhibit excellent catalytic activity in alkyne metathesis reactions of all kinds. Adduct 11 is sufficiently stable to be weighed in air and is therefore much easier to use than any of the established, structurally defined alkyne metathesis precatalysts known to date. This new system is compatible with a host of functional groups, including esters, amides, alkenes, carbamates, ethers, silyl ethers, sulfonates, thioethers, THP acetals, glycosides, ketones, enoates, thiophenes, pyridines, thiazoles, and nitro groups, and even accepts protected propargyl alcohols as substrates. It has been used for the preparation of key intermediates for bioactive natural products, such as gallicynoic acid I, homoepilachnene, epothilone A, cruentaren A, and a fully synthetic latrunculin analogue. However, 9 and 11 react with aldehydes and acid chlorides to give the corresponding nitrile derivatives.