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Organocatalytic Enantioselective Alkylation of Aldehydes with [Fe(bpy)3]Br2 Catalyst and Visible Light

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journal contribution
posted on 02.10.2015, 00:00 by Andrea Gualandi, Marianna Marchini, Luca Mengozzi, Mirco Natali, Marco Lucarini, Paola Ceroni, Pier Giorgio Cozzi
Catalytic amounts (2.5 mol %) of [Fe­(bpy)3]­Br2 complex in the presence of visible light and the MacMillan catalyst 3 (20 mol %) are highly effective in promoting an enantioselective organocatalytic photoredox alkylation of aldehydes with various α-bromo carbonyl compounds. Reaction yields of isolated compounds and enantioselectivities are very good and comparable to the ones obtained by [Ru­(bpy)3]2+, organic dyes, or semiconductors, in the presence of the same organocatalysts. The use of first-row, abundant, and cheap metals in photocatalyzed reactions can open new perspectives in stereoselective organic synthesis.