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Divergent Synthesis of alpha-Fluorinated Carbonyl and Carboxyl Derivatives by Double Electrophilic Activation of Amides

par Dubart, Amaury ;Evano, Gwilherm
Référence Organic letters, 23, page (8931-8936)
Publication Publié, 2021-10-26

Article révisé par les pairs

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Résumé :

A straightforward and divergent entry to alpha-fluorinated carbonyl and carboxyl derivatives is reported. Upon activation of amides with triflic anhydride and a 2-halo-pyridine and subsequent trapping of the resulting keteniminium ions with nucleophiles followed by a second electrophilic activation with NFSI and final hydrolysis, a range of amides can be transformed to alpha-fluorinated ketones, esters, and amides under mild conditions. Moreover, this reaction can be performed to yield enantioenriched products with a traceless chiral auxiliary.