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Journal Article

Cross-Metathesis of Terminal Alkynes


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

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

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Lhermet, R., & Fürstner, A. (2014). Cross-Metathesis of Terminal Alkynes. Chemistry - A European Journal, 20(41), 13188-13193. doi:10.1002/chem.201404166.

Cite as:
Terminal acetylenes are amongst the most problematic substrates for alkyne metathesis because they tend to undergo rapid polymerization on contact with a metal alkylidyne. The molybdenum complex 3 endowed with triphenylsilanolate ligands, however, is capable of inducing surprisingly effective cross-metathesis reactions of terminal alkyl acetylenes with propynyl(trimethyl)silane to give products of type R1–C≡CSiMe . This unconventional way of introducing a silyl substituent onto an alkyne terminus complements the conventional tactics of deprotonation/silylation and excels as an orthogonal way of alkyne protecting group chemistry for substrates bearing base-sensitive functionalities. Moreover, it is shown that even terminal aryl acetylenes can be cross-metathesized with internal alkyne partners. These unprecedented transformations are compatible with various functional groups. The need to suppress acetylene formation, which seems to be a particularly effective catalyst poison, is also discussed.