An efficient PIDA (phenyliodine(III) diacetate)-promoted positional selective CÀ H selenylations of indolines with diaryl diselenides has been developed. This transformation conducted under mild reaction conditions with a broad functional group tolerance, thus providing an efficient protocol to selenylated indolines. Preliminary mechanistic studies indicated a SET pathway was likely involved in this selenylation reaction.

This review summarizes recent advances in C–S and C–Se formations via transition metal-catalyzed C–H functionalization utilizing directing groups to control the site-selectivity.

A sustainable and highly efficient cobaltaelectro-catalyzed C–H/N–H functionalization with allenes was developed featuring electro-reductive hydrazide cleavage.

No abstract

A Brønsted acid catalysed regiodivergent phosphorylation of 2-indolylmethanols with diarylphosphine oxides has been established, which provides a brand-new strategy for accessing highly functionalized phosphorus-containing indoles with structural diversity. Under the catalysis of HOTs·H2O, 2-indolylmethanols undergo regioselective benzylic phosphorylation at room temperature to afford benzylic site phosphorylated indoles in good to high yields (29 examples, up to 98% yield), while C3-phosphorylated indoles are obtained in the presence of HOTf under heating conditions (16 examples, up to 83% yield). Preliminary mechanistic studies suggest that C3-phosphorylated indoles are possibly obtained partially from direct C3-phosphorylation and dominantly from a tandem benzylic phosphorylation/[1,3]-P migration/isomerization sequence from 2-indolylmethanols. Furthermore, the acidity of the Brønsted acid and the reaction temperature play a vital role in the [1,3]-P migration of benzylic phosphorylated indoles to form C3-phosphorylated indoles. This protocol serves as a good example for regioselective benzylic functionalization of 2-indolylmethanols.

A convenient and effective protocol for the ruthenium‐catalyzed C–H selenylations of benzamide was achieved under mild reaction conditions. The robust ruthenium catalyst tolerated a wide range of functional groups and set the stage for the preparation for diversely decorated benzamides. The amide directing group could be transferred to carboxylic acid, aldehyde and tetrazoles. Preliminary mechanistic study indicated a base‐assisted electrophilic‐type substitution C–H activation event.

An efficient ruthenium-catalyzed direct C−H selenylation of aryl acetic amides and esters has been achieved via distal weakly coordination. Notable features of this protocol including broad substrate scope, wide functional group tolerance, and good regioselectivity. In addition, diaryl disulfides were also successfully applied to this reaction under slightly modified conditions.

The first palladium(II)‐catalyzed direct ortho‐C(sp2)–H chalcogenations of N‐arylsulfonamide via weak coordination have been achieved, affording the corresponding mono‐chalocgenated products in good to excellent yields. This strategy features ligand/additive‐free conditions, broad substrate scope with excellent functional group tolerance and a high position selectivity.