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A SeCSe−Pd(II) Pincer Complex as a Highly Efficient Catalyst for Allylation of Aldehydes with Allyltributyltin

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journal contribution
posted on 07.07.2006, 00:00 by Qingwei Yao, Matthew Sheets
An air- and moisture-stable SeCSe−Pd(II) pincer complex was synthesized and found to catalyze the nucleophilic allylation of aldehydes with allyltributyltin. The allylation of a variety of aromatic and aliphatic aldehydes to give the corresponding homoallyl alcohols was performed at room temperature to 60 °C in yields ranging from 50% (for typical aliphatic aldehydes) to up to 97% (for aromatic aldehydes) using 5 × 10-3 to 1 mol % of the Pd catalyst. NMR spectroscopic study indicated that a σ-allylpalladium intermediate was formed and possibly functions as the nucleophilic species that undergoes addition to the aldehydes.