The manganese-catalyzed addition of C-2 position of indoles to maleimides has been achieved under additive-free conditions. The manganese catalyst exhibits excellent chemo- and regioselectivity, good functional group compatibility, and high catalytic efficiency. The substrate scope can also be extended to maleates, ethyl acrylate, 1,4-dihydro-1,4-epoxynaphthalene, pyrroles, and 2-phenylpyridine, which further demonstrates the universality of this straightforward approach.
The first nickel‐catalyzed ortho‐sulfonylation of C(sp2)–H bonds with sodium sulfinates directed by (pyridin‐2‐yl)isopropylamine (PIP‐amine) is described. This strategy exhibits a broad substrate scope and good functional group tolerance with high monosulfonylation selectivity. Besides arenes and heteroarenes, the reaction can also be extended to alkenes, providing diverse diaryl and alkyl aryl sulfones in high yields. Furthermore, a plausible Ni(I)/Ni(III) mechanism is outlined based on our experimental results and related precedents.magnified image
A copper‐promoted thiolation of C(sp2)–H bonds with disulfides was achieved by using 2‐amino alkylbenzimidazole (MBIP amine) as a new and removable N,N‐bidentate directing group. This strategy gives a variety of functionalized thioethers in moderate to excellent yields in a simple and efficient way. Importantly, the substrate scope is not limited to aromatic amides; diverse alkenyl amides are also compatible. Furthermore, this synthetic approach provides a potentially feasible way to achieve structural modification of related benzimidazole‐containing compounds through direct C–H activation.
A copper-catalyzed regioselective C2–H chlorination of indoles with para-toluenesulfonyl chloride (TsCl) is developed. Control experiments suggested that intermolecular single-electron-transfer processes might be involved in the reactions.
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