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A selective monodefluorinative alkylation of 3,3-difluorooxindoles is achieved. The reaction starts by the attack of a 4-dimethylaminopyrine-boryl radical to the carbonyl oxygen atom of 3,3-difluorooxindoles, followed by a spin-center shift to generate radical intermediates with the elimination of a fluoride anion. The subsequent radical addition to alkenes affords a range of 3-alkyl-fluorooxindoles products. The strategy offers access to C-3 functionalized oxindoles with wide substrate scope and tolerates a wide range of functional groups.

Here, an efficient Minisci reaction of heteroarenes and unactivated C(sp3)-H alkanes was achieved using inexpensive FeCl3 as a photocatalyst. The photogenerated chlorine radical contributed to the HAT of C-H and...

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