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Alkylation of Phosphinite/Phosphonite-Boranes via Temporary Protection of the P–H Bond

A new alkylation protocol for the synthesis of tertiary phosphonite­/phosphinite-boranes is developed. P-Alkylation products are obtained exclusively in moderate to very good yields from easily accessible (1-hydroxy-1-methylethyl)/(1-hydroxy-1-cyclohexyl) phosphonite/phosphinite-boranes upon reaction… Click to show full abstract

A new alkylation protocol for the synthesis of tertiary phosphonite­/phosphinite-boranes is developed. P-Alkylation products are obtained exclusively in moderate to very good yields from easily accessible (1-hydroxy-1-methylethyl)/(1-hydroxy-1-cyclohexyl) phosphonite/phosphinite-boranes upon reaction with a variety of electrophiles under mild conditions. The methodology opens up new synthetic routes for organophosphorus chemistry and offers access to valuable alkyl phosphonite/phosphinite-boranes. In contrast to previously reported oxidative removal–substitution sequences for the preparation of optically active phosphinite-boranes, our protocol provides a one-step procedure that occurs without loss of stereochemical information at phosphorus. This new approach provides a rather advantageous protocol when compared to direct alkylation methods (which may undergo P-epimerization) and occurs in a stereoselective manner even at 0 °C.

Keywords: phosphinite boranes; phosphinite; alkylation phosphinite; alkylation; phosphinite phosphonite; phosphonite phosphinite

Journal Title: Synthesis
Year Published: 2020

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