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  • Transition-Metal-Free alpha-Arylation of beta-Keto Amides via an Interrupted Insertion Reaction of Arynes
    Organic Letters, 2012
    Co-Authors: Kishor Mohanan, Yoann Coquerel, Jean Rodriguez
    Abstract:

    Direct alpha-arylation Reactions of secondary beta-keto amides with arynes, generated by fluoride-induced elimination of ortho-silyl aryltriflates, are described. The transformation 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, affording the proof of concept that arynes can be involved in enantioselective transformations.

  • transition metal free α arylation of β keto amides via an interrupted Insertion Reaction of arynes
    Organic Letters, 2012
    Co-Authors: Kishor Mohanan, Yoann Coquerel, Jean Rodriguez
    Abstract:

    Direct α-arylation Reactions of secondary β-keto amides with arynes, generated by fluoride-induced elimination of ortho-silyl aryltriflates, are described. The transformation 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, affording the proof of concept that arynes can be involved in enantioselective transformations.