Glaser coupling

The Glaser coupling is a type of coupling reaction. It is by far the oldest acetylenic coupling and is based on cuprous salts like copper(I) chloride or copper(I) bromide and an additional oxidant like oxygen. The base in its original scope is ammonia. The solvent is water or an alcohol. The reaction was first reported by Carl Andreas Glaser in 1869. He suggested the following process for his way to diphenylbutadiyne:

CuCl + PhC2H + NH3 → PhC2Cu + NH4Cl
4 PhC2Cu + O2 → 2PhC2C2Ph + 2Cu2O
Glaser coupling
Named after Carl Andreas Glaser
Reaction type Coupling reaction
Identifiers
Organic Chemistry Portal glaser-coupling
RSC ontology ID RXNO:0000098
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