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Rh(III)-catalyzed C7-alkylation of isatogens (indolin-3-one N-oxides) with malonic acid diazoesters has been developed. This strategy utilizes oxygen anion on the N-oxide group of isatogens as a directing group and successfully achieves the synthesis of a series of C7-alkylated isatogens with moderate to good yields (48–86% yields). Moreover, the N-oxides of isatogens can not only serve as the simple directing group for C7–H bond cleavage but also be deoxidized for easy removal.
Guan et al. (Fri,) studied this question.