Transition-Metal-Free alpha-Arylation of beta-Keto Amides via an Interrupted Insertion Reaction of Arynes - Aix-Marseille Université Access content directly
Journal Articles Organic Letters Year : 2012

Transition-Metal-Free alpha-Arylation of beta-Keto Amides via an Interrupted Insertion Reaction of Arynes

Yoann Coquerel
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Jean Rodriguez
  • Function : Correspondent author
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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.
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hal-00736636 , version 1 (28-09-2012)

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Kishor Mohanan, Yoann Coquerel, Jean Rodriguez. Transition-Metal-Free alpha-Arylation of beta-Keto Amides via an Interrupted Insertion Reaction of Arynes. Organic Letters, 2012, 14, pp.4686-4689. ⟨10.1021/ol302180v⟩. ⟨hal-00736636⟩
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