The other half of the Michaelis–Arbuzov reaction: A new synthetic route to tertiary phosphorus–carbon bond formation

A first-row transition metal assisted modification of the Michaelis–Arbuzov rearrangement has been discovered that allows the reaction to take place under ambient conditions using a mild phosphine nucleophile. This reaction has been used as a novel synthetic strategy for the assembly of P–C bonds in typically difficult to construct 3-methylpyridyl substituted phosphine and phosphonium ligands. Metal complexes of these ligands were characterized crystallographically. One of the products also contains the previously unknown pyridylFeCl3- species.

Graphical abstractA first-row transition metal assisted modification of the Michaelis–Arbuzov rearrangement has been discovered that allows the reaction to take place under ambient conditions using a mild phosphine nucleophile and has been used as a novel method for the construction of a new P–C bond.Figure optionsDownload full-size imageDownload as PowerPoint slide