A carbene transfer reaction has been studied to understand the nature of the tris(pentafluorophenyl)borane stabilized donor-acceptor carbene. For this, a carbonate (or dicarbonate) molecule has been employed resulting in an overall carbonate functionality transfer. The results show that the diazo-derived carbenic carbon displays an electrophilic character. This also presents an opportunity to develop future carbene transfer reactions using a multitude of unconventional nucleophiles with the tris(pentafluorophenyl)borane catalyst.

A novel method for chemoselective difunctinalization of activated alkynes for synthesizing 3-alkylated spiro[4,5]- trienones, thiaspiro[4,5]- trienones and spirolactams has been uncovered using photoredox catalysis under visible light conditions. The rarely...

The borylation of Csp3‐H bonds is a challenging transformation that is typically restricted to transition metal catalysis. Herein, we report the site‐selective metal‐free Csp3–H borylation of saturated cyclic amines. It is possible to selectively borylate piperidine derivatives at the α or β positions according to the reaction conditions. The mechanism was supported by NMR spectroscopy, calorimetry experiments and density functional theory (DFT) computations. It suggests that the piperidine is dehydrogenated by complexation with BBr3 to produce an enamine intermediate, which is in turn borylated at either the α or β position according to the reaction conditions.

The borylation of Csp3‐H bonds is a challenging transformation that is typically restricted to transition metal catalysis. Herein, we report the site‐selective metal‐free Csp3–H borylation of saturated cyclic amines. It is possible to selectively borylate piperidine derivatives at the α or β positions according to the reaction conditions. The mechanism was supported by NMR spectroscopy, calorimetry experiments and density functional theory (DFT) computations. It suggests that the piperidine is dehydrogenated by complexation with BBr3 to produce an enamine intermediate, which is in turn borylated at either the α or β position according to the reaction conditions.