Iron-catalyzed ring-opening azidation and allylation of O-heterocycles.

We have established the first catalytic C-C and C-N bond formation reactions of O-heterocycles (e.g., tetrahydrofuran, phthalane, and lactone derivatives) using iron trichloride as a catalyst in the presence of TMSN3 or allylsilanes accompanied by the ring opening of O-heterocycles. The reactions smoothly proceeded at room temperature to give the corresponding primary saturated alcohols from the 2-substituted tetrahydrofurans, ortho-substituted benzyl alcohols from phthalanes, and saturated carboxylic acids from lactones in high yields.

A simple and efficient oxidation of alcohols with ruthenium on carbon.

A simple, efficient, and environmentally-friendly heterogeneous Ru/C-catalyzed oxidation of secondary and primary alcohols without additives under an atmosphere of oxygen has been established.