A useful approach is developed for the synthesis of various structurally interesting spirocyclic sultams and heterobiaryls using a cross-dehydrogenative coupling strategy that features high atom and step economy. This method employs [Cp*RhCl2]2 as a catalyst and N-sulfonylimine, a weak coordinating group, as an efficient directing group to assist C-H activation. A number of the coupled products were converted into interesting molecules through further synthetic transformations.
A rhodium-catalysed direct C-H allylation of readily accessible N-sulfonyl ketimines with various allyl carbonates has successfully been achieved. The computational studies indicated that olefin insertion and β-oxygen elimination steps were involved in the catalytic cycle.
A useful method for the synthesis of ortho-olefinated ketimines from readily accessible cyclic N-sulfonyl ketimines and various olefins has been achieved. The reactions proceeded by Rh(III)-catalyzed, N-sulfonyl ketimine-directed C-H cleavage under aerobic conditions. Further synthetic transformations of the olefinic products led to interesting heterocyclic molecules.
RhIII‐catalyzed aryl C–H vinylation for the preparation of styrenes by using vinyl acetate, a commercially available and inexpensive compound, as the vinyl source was successfully realized. This method enables various aromatics including N‐sulfonyl ketimines, pyridines, azoles, and amides to be vinylated in moderate to good yields.
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