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Reference.org
Glaser coupling
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<p>The Glaser coupling is a type of <a href="/facts/Coupling_reaction/L464wvvk">coupling reaction</a>. It is by far one of the oldest coupling reactions and is based on copper compounds like <a href="/facts/Copper(I)_chloride/L8RgsAhF">copper(I) chloride</a> or <a href="/facts/Copper(I)_bromide/cKTKQjX9">copper(I) bromide</a> and an additional oxidant like air. The base used in the original research paper is <a href="/facts/Ammonia/MtLtJFtz">ammonia</a> and the solvent is water or an alcohol. The reaction was first reported by Carl Andreas Glaser [de] in 1869. He suggested the following process on his way to <a href="/facts/Diphenylbutadiyne/k9vFkpIe">diphenylbutadiyne</a>: </p> CuCl + PhC2H + NH3 → PhC2Cu + NH4Cl 4 PhC2Cu + O2 → 2PhC2C2Ph + 2Cu2O