Telluride-mediated aldehyde methylenation

In the presence of dibutyl telluride, iodomethyl triphenylphosphonium iodide reacts with aldehydes, in accordance with a Wittig-type olefmation, giving methylenation products.  

Methylenation reaction (typical procedure) A mixture of iodomethyl triphenylphosphonium iodide (0.530 g, 1.0 mmol), dibutyl telluride (0.242 g, 1.0 mmol) and p-bromoben-zaldehyde (0.096 g, 0.5 mmol) in THF (5 mL) is heated under reflux for 30 h, then cooled and filtered. The residue is purified by TLC, giving p-bromostyrene (0.080 g (87%)). 

Suzuki, H. Manabe, H. Inouye, M. Nippon Kagakn Kaishi 1987, 1485. 

Suzuki, H. Nishioka, Y. Padmanabhan, S. Ogawa, T. Chem. Lett. 1988, 727. 

---