Frustrated Lewis pairs , synthesis

Selective C—H activations using frustrated Lewis pairs AppHcations in organic synthesis 13TCC(334)171. 

SCHEME 4.319 Synthesis of frustrated Lewis acid-base pairs [433]. 

One of the more novel synthetic approaches to the synthesis of vinylphosphines entailed the addition of alkynes to a functionalized tertiary phosphine (Scheme 4.319) [433]. These compounds are part of a special class of compounds that contain an intramolecnlar frustrated Lewis acid-base pair (FLP). These FLPs have been used to react with small molecules such as hydrogen and carbon dioxide. The P—C bond-forming reaction was operationally trivial and consisted of mixing the aUcyne with the specialized precursor in a hydrocarbon solvent for 1 h. The product precipitated and was separated by simple filtration. Although the substrate scope for this reaction is limited at present, this approach does provide a pathway to an intriguing class of vinylphosphines. 

---