Our last blog assignment for Organic Chemistry was to go to Christina White’s (U. Illinois) webpage and find a publication to read and comment on. The article I chose was titled, A Sulfoxide-Promoted, Catalytic Method for the Regioselective Synthesis of Allylic Acetates from Monosubstituted Olefins via C-H Oxidation. The article states that sulfoxide ligation to Pd(II) salts is shown to selectively promote C-H oxidation opposed to Wacker oxidation chemistry and to control the regioselectivity in the C-H oxidation products. Also that using benzoquinone as the stoichiometric oxidant and 10 mol % of Pd(OAc)2 or Pd(O2CCF3)2 as the catalyst in a DMSO/AcOH (1:1) solution was found to be compatible with a wide range of functionality, which was shown in Table 2 in the article. The table shows amides, esters, and ethers that was compatible with the solution. I thought this table was useful because it talked about amides, esters and ethers that we have already learned in pervious chapters. The article also explores the potential role of sulfoxide as a ligand in promoting the palladium(II) catalyzed C-H oxidation pathway, and bis-sulfoxide palladium(II), this was shown in Table 1 of the article. These results demonstrated for the first time that sulfoxide ligation of Pd(II) salts can promote C-H acetates in useful yields, which was also shown in Table 2. Overall, I found this article very interesting and very informative. I also found that this article talked about organopalladium, which are compounds that contain a carbon-palladium bond that are prepared in situ during the course of a reaction, from another palladium regent such as Pd(OAC)2, which was in chapter 26. Lastly, the pictures wouldn’t let me copy them, but are easily viewed in the article.
Resources:
Chen, Mark S. A Sulfoxide-Promoted, Catalytic Method for the Regioselective Synthesis of Allylic Acetates from Monosubstituted Olefins via C-H Oxidation. JACS, 2004, 126, 1346-1347. http://www.scs.illinois.edu/white/index.php?p=publications (accessed May 15, 2004)
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