Skip to Main content Skip to Navigation
Journal articles

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

Kishor Mohanan 1 Yoann Coquerel 2, * Jean Rodriguez 2, * 
* Corresponding author
2 STeRéO
ISM2 - Institut des Sciences Moléculaires de Marseille
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.
Document type :
Journal articles
Complete list of metadata

https://hal.archives-ouvertes.fr/hal-00736636
Contributor : Gaelle Chouraqui Connect in order to contact the contributor
Submitted on : Friday, September 28, 2012 - 4:35:44 PM
Last modification on : Tuesday, December 14, 2021 - 8:36:11 AM

Identifiers

Collections

Citation

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

Share

Metrics

Record views

35