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Updated: Dec 14, 2025
A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
Fast and Chemoselective Addition of Highly Polarized Lithium Phosphides Generated in Deep Eutectic Solvents to
Luciana Cicco1, Alba Fombona-Pascual2,3, Alba Sánchez-Condado2
1Dipartimento di Farmacia-Scienze del Farmaco, Università di Bari "Aldo Moro", Consorzio C.I.N.M.P.I.S., Via E. Orabona, 4, 70125, Bari, Italy.
Abstract:
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 ) by n-BuLi. The subsequent addition of in-situ generated LiPR2 to aldehydes or epoxides proceeded quickly and chemoselectively, thereby allowing the straightforward access to the corresponding α- or β-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.
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