We report the development of a photocatalytic strategy for the synthesis of β-functionalized unsymmetrical 1,4-, 1-6 and 1,7-diketones from aroyl chlorides and unactivated alkenes at room temperature. The mild reaction conditions not only tolerate a wide range of functional groups and structural moieties, but also enable migration of a variety of distal groups including (hetero)arenes, nitrile, aldehyde, oxime-derivative, and alkene. The efficiency of chirality transfer, factors that control the distal-group migration, and synthesis of carbo- and heterocycles from the diketones are also described. Mechanistic studies suggest a reaction pathway involving a photocatalytic radical aroylation of unactivated alkenes followed by a distal-group migration, oxidation, and deprotonation to afford the desired diketones.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8147874 | PMC |
| http://dx.doi.org/10.1021/acscatal.9b03570 | DOI Listing |
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