Efficient synthesis of α-amino-vinylphosphine oxides from alkyl nitriles via manganese-catalyzed phosphinoenamination.

A protocol for the synthesis of α-amino-vinylphosphine oxides by phosphinoenamination reaction between alkyl nitriles and phosphine oxides was developed. The combination of Mn(OAc)2 as a Lewis acid and guanidine as a Lewis base was found to be an efficient catalytic system for this reaction. A series of alkyl nitriles and phosphine oxides are compatible with this conversion, furnishing the desired products in up to 95% yield under mild conditions. Furthermore, this method demonstrates the capability of gram-scale synthesis.

Visible-light-induced C(sp3)-C(sp3) bond formation via radical/radical cross-coupling.

Radical/radical cross-coupling remains challenging due to diffusion control issues. Herein, we report a visible-light-induced radical/radical cross-coupling reaction of quaternary ammonium salts and Hantzschs via C-N and C-C bond cleavage. The current synthetic approach furnishes 1,2-diphenylethanes in moderate to good yields and provides a method for the construction of the C(sp3)-C(sp3) bond.

Bromide ion promoted practical synthesis of phosphinothioates of sulfinic acid derivatives and H-phosphine oxides.

A feasible method for the synthesis of phosphinothioates from sulfinic acid derivatives and phosphine oxides is described. This reaction can be carried out in an open flask at room temperature and in an aqueous medium. The scope of the sulfinic acid derivatives is extensive, with a wide range of sulfinate esters, sulfinic acids, and sodium sulfinates compatible with these conditions, with good to excellent yields of phosphinothioates. In addition, a gram-scale synthesis with this reaction is achieved. A mechanism of this procedure was proposed.