Transition-Metal-Free Photoredox Phosphonation of Aryl C-N and C-X Bonds in Aqueous Solvent Mixtures.

Herein, we present an efficient and mild methodology for the synthesis of aromatic phosphonate esters in good to excellent yields using 10-phenothiazine, an inexpensive commodity chemical, as a photoredox catalyst. The reaction exhibits wide functional group compatibility enabling the transformation in the presence of ketone, amide, ester, amine, and alcohol moieties. Importantly, the reaction proceeds using a green solvent mixture primarily composed of water, thus lowering the environmental footprint of this transformation compared to current methods.

Synthesis of Imide and Amine Derivatives via Deoxyamination of Alcohols Using -Haloimides and Triphenylphosphine.

A deoxyamination methodology of activated and unactivated alcohols is presented. The reaction is mediated by phosphonium intermediates generated from -haloimides and triphenylphosphine. The protocol allows for the synthesis of phthalimide and amine derivatives in moderate to good yields at room temperature.