A new ruthenium catalytic system was developed for the construction of a C(sp(2))-Se bond with the assistance of directing groups. This protocol features mild reaction conditions, wider substrate scope, and convenient late-stage selenylation of bioactive molecules.

Stereoselective functionalization of the adamantyl bridge methylene C­(sp3)–H bonds is a rather appealing, yet challenging strategy due to the bulky and unactivated nature. Here we present a palladium-catalyzed C­(sp3)–H arylation/hetereoarylation of the antivirus drug rimantadine with the picolinamide moiety as the bidentate directing group and a mono-N-protected amino acid (MPAA) as the ligand. Multisubstituted rimantadine substrates and diverse aryl/heteroaryl iodides are well tolerated, and a series of optically pure arylated rimantadine derivatives have been synthesized in high regio- and diastereoselectivity that provides ample compound space for further pharmaceutical research.

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A number of N‐heterocycles have been tested as directing group in the novel Ru‐catalyzed regioselective ortho‐selenylation of benzene featuring 2‐pyridinyl and 1‐pyrazolyl groups as most promising candidates that have been further examined in a broad variety of arenes.