Catalytic Photoredox Allylation of Aldehydes Promoted by a Cobalt Complex
Andrea Gualandi, Giacomo Rodeghiero, Rossana Perciaccante, Thomas Paul Jansen, Cristina Moreno‐Cabrerizo, Charles Foucher, Marianna Marchini, Paola Ceroni, Pier Giorgio Cozzi
Abstract
Abstract The preparation of homoallylic alcohols by addition of organometallic allyl compounds to carbonyls is an important strategy in organic chemistry. Allylating organometallic cobalt species can be generated employing stoichiometric quantities of Zn acting as reductant. To avoid the employment of stoichiometric amount of Zn, we have developed an allylation reaction of aromatic and aliphatic aldehydes promoted by photoredox catalysis in the presence of a cobalt complex, and we present herein a full account of our research. In the presence of the abundant CoBr 2 (10 mol %), 4,4′‐di‐ tert ‐butyl‐2,2′‐dipyridyl (dtbbpy, 10 mol %), allyl acetate (3 equiv.), [Ir(dtbbpy)(ppy) 2 ]PF 6 (ppy=2‐phenylpyridine, 2 mol %), and N , N ‐diisopropylethylamine (4 equiv.), an allylation of aldehydes is taking place, in moderate to good yields. Substrates scope, limitations, and photophysical investigations of this new process are reported. magnified image