|
|||||
|
|
Friedel–Crafts Reaction of Benzyl Fluorides: Selective Activation of CF Bonds as Enabled by Hydrogen Bonding |
|
| Authors: | Pier Alexandre Champagne Yasmine Benhassine Justine Desroches Prof Jean‐François Paquin |
| Institution: | Canada Research Chair in Organic and Medicinal Chemistry, CCVC, PROTEO, Département de chimie, Université Laval, 1045 Avenue de la Médecine, Pavillon Alexandre‐Vachon, Québec, Québec, G1V 0A6 (Canada) |
| Abstract: | A Friedel–Crafts benzylation of arenes with benzyl fluorides has been developed. The reaction produces 1,1‐diaryl alkanes in good yield under mild conditions without the need for a transition metal or a strong Lewis acid. A mechanism involving activation of the C? F bond through hydrogen bonding is proposed. This mode of activation enables the selective reaction of benzylic C? F bonds in the presence of other benzylic leaving groups. |
| Keywords: | arenes benzyl fluorides C F activation Friedel– Crafts reaction hydrogen bonds |