[1,2-Bis(phenylsulfinyl)ethane]palladium Acetate

Introduction

[1,2-Bis(phenylsulfinyl)ethane]palladium acetate 1, the ‘White catalyst’, was developed by M. Christina White and co-workers at the University of Illinois-Urbana. It has been shown to be an excellent, air-stable catalyst for the functionalization of allylic carbon centers. [¹] The bis-­sulfoxide palladium(II) catalyst participates in a number of important reactions including allylic C-H oxidation, [²] inter- and intramolecular alkylations, [³] sequential hydrocarbon functionalization, [4] macrolactonizations, [5] allylic C-H amination [6] and intermolecular oxidative Mizoroki-Heck reactions. [7] These useful transformations allow for rapid access to an array of synthetically useful moieties, such as allylic carboxylates, macrocycles, and amino alcohol deri­vatives.

Figure 1  White catalyst

Bis-sulfoxide palladium(II) acetate complex 1 is commercially available and can also be prepared via routine metal complexation with 1,2-bis(phenylmethanesulfinyl)ethane in dichloromethane at 40 ˚C. [8]

References

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