Direct functionalization of benzylic C–Hs with vinyl acetates via Fe-catalysis

Abstract

Direct cross-coupling to construct sp3 C-sp3 C bonds via Fe-catalyzed benzylic C-H activation with 1-aryl vinyl acetate was developed.

Iron Catalysis in Organic Synthesis

“…The oxidative coupling of diarylmethanes with vinyl acetates was achieved using catalytic amounts of iron(II) chloride and di-tertbutyl peroxide as oxidant (Scheme 292). 556 The reaction proceeded under solvent-free conditions at elevated temperature to afford β-diaryl ketones. Two possible mechanistic pathways, a radical process and a cationic process, have been proposed, both starting with the formation of a benzylic radical via hydrogen abstraction.…”

Iron‐Catalyzed Direct Arylation of Unactivated Arenes with Aryl Halides

“…[57] Many other oxidative coupling reactions, which involve CÀH activation using iron catalysts in the presence of stoichiometric amounts of oxidants, have also been reported. [58][59][60][61] However, to the best of our knowledge, no example of Fecatalyzed cross-coupling between Ar 1 X and Ar 2 H has been reported (Scheme 1). Herein, we report the development of novel Fe-catalyzed cross-coupling reactions between electrophilic Ar 1 X (X = I, Br, Cl) and unactivated Ar 2 H coupling partners.…”

Iron-Catalyzed Cross-Dehydrogenative-Coupling Reactions

“…Iron-catalyzed direct functionalization of benzylic C-H bonds with vinyl acetates was also achieved by Shi and coworkers in 2009 [43]. The reaction ran very smoothly to get the cross-coupling products in good to excellent yields in the presence of FeCl 2 Bu were used as an oxidant.…”