The Meerwein arylation is an organic reaction involving the addition of an aryldiazonium 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.
In a general scope a Meerwein arylation is any reaction between an aryl radical and an alkene.[3] The initial intermediate is an aryl enthenyl radical which can react with many trapping reagents such as hydrogen or halogens or with those based on nitrogen or sulfur.
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]
Metal free meerwein arylation
See also
Roskamp reaction – also sees substitution of a diazonium compound by a carbon centre
^Meerwein, Hans; Buchner, Eberhard; van Emster, Konrad (1939). "Über die Einwirkung aromatischer Diazoverbindungen auf α,β-ungesättigte Carbonylverbindungen". J. Prakt. Chem. (in German). 152 (7–10): 237–266. doi:10.1002/prac.19391520705.
^Kürti, Laszlo; Czakó, Barbara (2005). Strategic Applications of Named Reactions in Organic Synthesis: Background and Detailed Mechanisms. Elsevier Academic Press. ISBN9780124297852.
^Molinaro, Carmela; Mowat, Jeffrey; Gosselin, Francis; O'Shea, Paul D.; Marcoux, Jean-François; Angelaud, Rémy; Davies, Ian W. (2007). "A Practical Synthesis of α-Aryl Methyl Ketones via a Transition-Metal-Free Meerwein Arylation". J. Org. Chem.72 (5): 1856–1858. doi:10.1021/jo062483g. PMID17263583.
