Catalyst- and Halogen-Free Regioselective Friedel-Crafts alpha-Ketoacylations

Kishor Mohanan (1) , Marc Presset (1) , Damien Mailhol (1) , Yoann Coquerel (1) , Jean Rodriguez (1)

1 STeRéO

Highly regio- selective and efficient catalyst- and halogen-free Friedel-Crafts alpha-ketoacy- lation reactions leading to heterocycles functionalized with a very versatile 1,3- diketone moiety are described. The reactions rely on microwave-assisted domino Wolff rearrangement/Friedel- Crafts sequences from 2-diazo-1,3- diketones via transient, highly reactive alpha-keto ketene intermediates.

Mots clés: Heterocycles; Regioselectivity; Diazo compounds; Acylations; Domino reactions; Microwave chemistry

Domaines: Chimie organique

Kishor Mohanan, Marc Presset, Damien Mailhol, Yoann Coquerel, Jean Rodriguez. Catalyst- and Halogen-Free Regioselective Friedel-Crafts alpha-Ketoacylations. Chemistry - A European Journal, 2012, 18, pp.9217-9220. ⟨10.1002/chem.201201027⟩. ⟨hal-00736640⟩