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. [1][2] The reaction was first reported by Carl Andreas Glaser in 1869.
In 1882 Adolf von Baeyer used the method to synthesise indigo dye from cinnamic acid.[3][4]
See Also
- Cadiot–Chodkiewicz coupling - Another alkyne coupling reaction catalysed by copper (I).
- Sonogashira coupling - Pd/Cu catalysed coupling of an alkyne and an aryl or vinyl halide
- Castro–Stephens coupling - A cross-coupling reaction between a copper(I) acetylide and an aryl halide
References
- ↑ Glaser, Carl. "Untersuchungen über einige Derivate der Zimmtsäure". Annalen der Chemie und Pharmacie 154 (2): 137–171. doi:10.1002/jlac.18701540202.
- ↑ Glaser, C. "Beiträge zur Kenntniss des Acetenylbenzols". Berichte der deutschen chemischen Gesellschaft 2 (1): 422–424. doi:10.1002/cber.186900201183.
- ↑ Baeyer, Adolf. "Ueber die Verbindungen der Indigogruppe". Berichte der deutschen chemischen Gesellschaft 15 (1): 50–56. doi:10.1002/cber.18820150116.
- ↑ Johansson Seechurn, Carin C. C.; Kitching, Matthew O.; Colacot, Thomas J.; Snieckus, Victor (21 May 2012). "Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize". Angewandte Chemie International Edition 51 (21): 5062–5085. doi:10.1002/anie.201107017.