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 [de] in 1869.^[1]^[2] He suggested the following process on his way to diphenylbutadiyne:

CuCl + PhC₂H + NH₃ → PhC₂Cu + NH₄Cl

4 PhC₂Cu + O₂ → 2PhC₂C₂Ph + 2Cu₂O

^ Glaser, Carl (1870). "Untersuchungen über einige Derivate der Zimmtsäure" [Studies on some derivatives of cinnamic acid]. Annalen der Chemie und Pharmacie (in German). 154 (2): 137–171. doi:10.1002/jlac.18701540202.
^ Glaser, C. (1869). "Beiträge zur Kenntniss des Acetenylbenzols". Berichte der Deutschen Chemischen Gesellschaft. 2 (1): 422–424. doi:10.1002/cber.186900201183.

[1] Glaser, Carl (1870). "Untersuchungen über einige Derivate der Zimmtsäure" [Studies on some derivatives of cinnamic acid]. Annalen der Chemie und Pharmacie (in German). 154 (2): 137–171. doi:10.1002/jlac.18701540202.

[2] Glaser, C. (1869). "Beiträge zur Kenntniss des Acetenylbenzols". Berichte der Deutschen Chemischen Gesellschaft. 2 (1): 422–424. doi:10.1002/cber.186900201183.

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