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: yoann.coquerel
univ-amu.fr;
jean.rodriguezuniv-amu.fr
K. Mohanan, Y. Coquerel, J. Rodriguez, Org. Lett., 2012, 14, 4686-4689.
DOI: 10.1021/ol302180v
see article for more reactions
Abstract
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
