Meerwein arylation
| Meerwein arylation | |
|---|---|
| Named after | Hans Meerwein |
| Reaction type | Coupling reaction |
The Meerwein arylation is an
diazonium salt (ArN2X) to an electron-poor alkene usually supported by a metal salt.[1] The reaction product is an alkylated arene compound. The reaction is named after Hans Meerwein
, one of its inventors who first published it in 1939.
An
free radical addition. In the primary reaction product the intermediate alkyl radical is then captured by the diazonium counterion X which is usually a halogen or a tetrafluoroborate. In a subsequent step an elimination reaction liberates HX (for instance hydrochloric acid) and an aryl vinyl compound is formed. The reaction mechanism from the arene's view ranks as a radical-nucleophilic aromatic substitution
.
In a general scope a Meerwein arylation is any reaction between an
.Scope
A reported reaction of alkene
reduces the newly formed double bond.[6]
In a novel kilogram-scale metal-free Meerwein arylation the diazonium salt is formed from 2-nitroaniline, the alkene isopropenyl acetate is an adduct of propyne and acetic acid and the reaction product 2-nitrophenylacetone:[7]
See also
- Roskamp reaction – also sees substitution of a diazonium compound by a carbon centre
- Heck-Matsuda reaction– palladium catalysed version
References
- .
- ISBN 9780124297852.
- PMID 19086045.
- ; Collected Volumes, vol. 6, p. 21.
- ; Collected Volumes, vol. 4, p. 727.
- ; Collected Volumes, vol. 7, p. 105.
- PMID 17263583.