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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.coquereluniv-amu.fr; jean.rodriguezuniv-amu.fr

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

DOI: 10.1021/ol302180v (free Supporting Information)


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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.

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Key Words

α-arylation


ID: J54-Y2012-3000