Organic Chemistry Portal



Transition-Metal-Free α-Arylation of β-Keto Amides via an Interrupted Insertion Reaction of Arynes

Kishor Mohanan, Yoann Coquerel* and Jean Rodriguez*

*Aix-Marseille Université, CNRS, iSm2 UMR 7313, Service 531, 13397 Marseille cedex 20, France, Email:;

K. Mohanan, Y. Coquerel, J. Rodriguez, Org. Lett., 2012, 14, 4686-4689.

DOI: 10.1021/ol302180v (free Supporting Information)

see article for more reactions


A direct α-arylation of secondary β-keto amides with arynes, generated by fluoride-induced elimination of ortho-silyl aryltriflates, proceeds via an interrupted insertion reaction of arynes and leads to densely functionalized aromatic compounds exhibiting a chiral ‘all carbon' quaternary center under transition-metal-free conditions. An organocatalytic asymmetric version of the reaction also proved possible.

see article for more examples

Key Words


ID: J54-Y2012-3000