Hydrostannylation of Red Phosphorus: A Convenient Route to Monophosphines

Abstract

The preparation of valuable and industrially relevant organophosphorus compounds currently depends on indirect multistep procedures involving difficult-to-handle white phosphorus as a common P atom source. Herein, we report a practical and versatile method for the synthesis of a variety of monophosphorus compounds directly from the bench-stable allotrope red phosphorus (P_red ). The relatively inert P_red was productively functionalised by using the cheap and readily available radical reagent tri-n-butyltin hydride, and subsequent treatment with electrophiles yields useful P₁ compounds. Remarkably, these transformations require only modest inert-atmosphere techniques and use only reagents that are inexpensive and commercially available, making this a convenient and practical methodology accessible in most laboratory settings.