Siladifluoromethylation and Deoxo-trifluoromethylation of PV -H Compounds with TMSCF3 : Route to PV -CF2- Transfer Reagents and P-CF3 Compounds

Organic Letters
Vinayak KrishnamurtiG K Surya Prakash

Abstract

A method for siladifluoromethylation of dialkyl phosphonates and secondary phosphine oxides with TMSCF3 to produce nucleophilic PV-CF2- transfer reagents is disclosed, with multigram scale reactions included. Condition-dependent divergent reactivity under the established conditions is demonstrated by the formation of trifluoromethylphosphines. Both one-pot transformations are operationally simple and employ inexpensive materials. Mechanistic investigations suggest the divergent reactivity originates from a common intermediate, with Li+ concentration directing the chemoselectivity.

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