Mild, Selective Ru-Catalyzed Deuteration Using D O as a Deuterium Source.

A method for the selective deuteration of polyfunctional organic molecules using catalytic amounts of [RuCl (PPh ) ] and D O as a deuterium source is presented. Through variation of additives like CuI, KOH, and various amounts of zinc powder, orthogonal chemoselectivities in the deuteration process are observed. Mechanistic investigation indicates the presence of different, defined Ru-complexes under the given specific conditions.

A Cyanide-Free Synthesis of Acylcyanides through Ru-Catalyzed C(sp)-H-Oxidation of Benzylic Nitriles.

A practical method for generation of acylcyanides devoid of any external cyanide sources is presented that relies on a mild Ru-catalyzed selective C-H-oxidation of benzylic nitriles. The starting materials are smoothly generated through condensation of the corresponding carboxylic acid amides using silanes. The obtained acylcyanides can be employed in a plethora of transformation as exemplified to some larger extend in the sequence of C-H-oxidation-Tischenko-rearrangement for the generation of structurally diverse benzoyloxycyanohydrines.