Playing Reversi with H and N: A copper‐catalyzed intermolecular regioselective hydroamination of styrenes with polymethylhydrosiloxane and hydroxylamine derivatives has been developed. The catalysis accommodates challenging β‐substituted substrates. Moreover, the chiral biphosphine‐ligated copper complex successfully forms benzylamines with good enantiomeric ratios.

The rhodium-catalyzed oxidative coupling of aromatic imines with alkynes effectively proceeds via regioselective C-H bond cleavage to produce indenone imine and isoquinoline derivatives.

Chloroamine serves as an efficient amination reagent to the heteroaromatic C-H bond of azole under copper catalysis even at room temperature. This catalysis enables a rapid and concise construction of aminoazoles of great interest in biological and medicinal chemistry.

Oxidative coupling of primary, secondary, and tertiary benzamides with internal alkynes proceeds efficiently under rhodium catalysis to selectively give the corresponding 1:1 and 1:2 coupling products, accompanied by C–H and/or N–H bond cleavages. Some of the products exhibit intense fluorescence in the solid state.

A Cu-catalyzed regioselective and stereospecific aminoboration of styrenes with bis(pinacolato)diboron and O-benzoyl-N,N-dialkylhydroxylamines that delivers the corresponding β-aminoalkylboranes in good yields has been developed. The Cu catalysis enables introduction of both amine and boron moieties to C-C double bonds simultaneously in a syn fashion. Moreover, the use of a chiral biphosphine ligand, (S,S)-Me-Duphos, provides a catalytic enantioselective route to optically active β-aminoalkylboranes.

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A copper-mediated C6-selective dehydrogenative heteroarylation of 2-pyridones with 1,3-azoles has been developed. The reaction proceeded smoothly by twofold C-H cleavage even in the absence of noble-metal catalysts. The observed site selectivity was directed by a pyridyl substituent on the nitrogen atom of the pyridone ring. This directing group was readily removed after the coupling event, thus leading to 2-pyridone derivatives with a free N-H group. Moreover, in some cases, catalytic turnover of the Cu salt was also possible with the ideal terminal oxidant: molecular oxygen in air.