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Amino groups are common in both natural and synthetic compounds and offer a very attractive class of endogenous handles for bioconjugation. However, the ability to differentiate two types of amino groups and join them with high hetero‐selectivity and efficiency in a complex setting remains elusive. Herein, we report a new method for bioconjugation via one‐pot chemoselective clamping of two different amine nucleophiles using a simple ortho‐phthalaldehyde (OPA) reagent. Various α‐amino acids, aryl amines, and secondary amines can be crosslinked to the ϵ‐amino side chain of lysine on peptides or proteins with high efficiency and hetero‐selectivity. This method offers a simple and powerful means to crosslink small molecule drugs, imaging probes, peptides, proteins, carbohydrates, and even virus particles without any pre‐functionalization. [ABSTRACT FROM AUTHOR]

A simple and efficient visible‐light‐promoted selenylation/cyclization of enaminones have been realized for the practical synthesis of 3‐selanyl‐4H‐chromen‐4‐ones. This reaction is performed in the mild conditions, no transition metal catalyst or photocatalysts and no additional oxidants are required. In addition, the 3‐selanyl‐4H‐chromen‐4‐ones could be easily converted to selanyl‐functionalized pyrimidines by reacting with benzamidine substrates. [ABSTRACT FROM AUTHOR]

A practical method for the synthesis of selenylsubstituted indolo[2,1‐a]isoquinolin‐6(5H)‐ones through Fe(OTf)3‐promoted tandem selenylation/cyclization of 2‐arylindoles was developed. In this transformation, new C−Se bond and C−C bond were constructed simultaneously under mild conditions. [ABSTRACT FROM AUTHOR]

A metal‐free and efficient visible‐light‐induced spirocyclization of indolyl‐ynones with diselenides at room temperature under air atmosphere to prepare 3‐selenospiroindolenines in moderate to good yields has been developed. The resulting products were tested for in vitro anticancer activity by MTT assay, and compounds 3 c and 3 e showed potent cancer cell‐growth inhibition activities. [ABSTRACT FROM AUTHOR]