PhSeZn-halides explained

PhSeZn-halides (Santi's reagent) is a class of chemical compounds with general formula PhSeZnX (X = Cl, Br). This is the first example of bench stable zinc selenolates with a remarkable nucleophilic reactivity under on-water conditions. The synthesis and application of these reagents were first reported by Dr. Claudio Santi of the University of Perugia in 2008.^[1] In 2016, the lead compound (PhSeZnCl) becomes commercially available.^[2]

Laboratory preparation

PhSeX + Zn → PhSeZnX^[3]

References

1. Santi C., Santoro S., Battistelli B., Testaferri L., Tiecco, M. Preparation of the First Bench‐Stable Phenyl Selenolate: an Interesting “On Water” Nucleophilic Reagent. Eur. J. Org. Chem. 2008, 5387–5390 https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.200800869
2. Web site: Phenylselenozinc chloride 766089. Sigma-Aldrich.
3. Book: Santi, C.. 15 September 2011. John Wiley & Sons, Ltd. 10.1002/047084289x.rn01352. Encyclopedia of Reagents for Organic Synthesis. 978-0471936237. Phenylselenenylzinc Halides.