Fast and Chemoselective Addition of in Deep Eutectic Solvent Generated Highly Polarized Lithium Phosphides (LiPR2) to Aldehydes and Epoxides at Room Temperature and Under Air.

Highly polarized lithium phosphides (LiPR2) were synthesized, for the first time, in deep eutectic solvents as sustainable reaction media, at room temperature and in the absence of protecting atmosphere, through direct deprotonation of both aliphatic and aromatic secondary phosphines (HPR2) byn-BuLi. The subsequent addition of in-situ generated LiPR(2)to aldehydes or epoxides proceeded quickly and chemoselectively, thereby allowing the straightforward access to the corresponding alpha- or beta-hydroxy phosphine oxides, respectively, under air and at room temperature (bench conditions), which are traditionally considered as textbook-prohibited conditions in the field of polar organometallic chemistry of s-block elements.