Cadiot–Chodkiewicz coupling

<p>The Cadiot–Chodkiewicz coupling in <a href="/facts/Organic_chemistry/djxhxaNg">organic chemistry</a> is a <a href="/facts/Coupling_reaction/L464wvvk">coupling reaction</a> between a terminal <a href="/facts/Alkyne/VHI4N5Wo">alkyne</a> and a haloalkyne <a href="/facts/Catalyzed/LPBS7TQC">catalyzed</a> by a copper(I) salt such as <a href="/facts/Copper(I)_bromide/cKTKQjX9">copper(I) bromide</a> and an <a href="/facts/Amine/JvfYJfP6">amine</a> <a href="/facts/Base_(chemistry)/M9wA7qeM">base</a>. The reaction product is a 1,3-diyne or di-<a href="/facts/Alkyne/VHI4N5Wo">alkyne</a>.
</p><p>The <a href="/facts/Reaction_mechanism/9lanyVuy">reaction mechanism</a> involves <a href="/facts/Deprotonation/SmUSh369">deprotonation</a> by base of the terminal alkyne proton followed by formation of a <a href="/facts/Copper(I)_acetylide/SJeUHJQJ">copper(I) acetylide</a>. A cycle of <a href="/facts/Oxidative_addition/kPNIb4LB">oxidative addition</a> and <a href="/facts/Reductive_elimination/H2SXpH0n">reductive elimination</a> on the copper centre then creates a new carbon-carbon bond.
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Cadiot–Chodkiewicz coupling open-in-new

Cadiot–Chodkiewicz coupling