Glaser coupling

Glaser coupling
Named after Carl Andreas Glaser
Reaction type Coupling reaction
Identifiers
Organic Chemistry Portal glaser-coupling
RSC ontology ID RXNO:0000098

The Glaser coupling is a type of coupling reaction. It is by far one of the oldest coupling reactions and is based on copper compounds like copper(I) chloride or copper(I) bromide and an additional oxidant like air. The base used in the original research paper is ammonia and the solvent is water or an alcohol. The reaction was first reported by Carl Andreas Glaser in 1869. He suggested the following process on his way to diphenylbutadiyne:

CuCl + PhC2H + NH3 → PhC2Cu + NH4Cl
4 PhC2Cu + O2 → 2PhC2C2Ph + 2Cu2O
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