Palladium-Catalyzed Reaction of Aryl Iodides with Acetic Anhydride. A Carbon Monoxide-Free Synthesis of AcetophenonesSandro Cacchi,* Giancarlo Fabrizi, Federica Gavazza, and Antonella GoggiamaniOrg. Lett., 5 (3), 289 -291, 2003 (http://pharmacist.the-hive.tripod.com/acetophen.pdf)
(http://pharmacist.the-hive.tripod.com/acetophen.pdf)
DOI:
10.1021/ol027243b S1523-7060(02)07243-7 (http://dx.doi.org/10.1021/ol027243b%20S1523%2D7060%2802%2907243%2D7)
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000462963-file_h4ro.gif)Abstract: The palladium-catalyzed reaction of aryl iodides with acetic anhydride provides a straightforward and experimentally simple carbon monoxide-free route to acetophenones. The reaction tolerates a wide range of functionalized aryl iodides. Acetophenones are isolated in excellent yield with a variety of neutral, slightly electron-rich, and slightly electron-poor aryl iodides, whereas moderate yields are obtained with aryl iodides containing strongly electron-withdrawing substituents.
Nifty, buy does it really offer any significant advantages over Friedel-Crafts acylation (using Polyphosphoric acid and GAA)?
Not really, but it's just another possibility...
