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Acetophenones from Aryl Iodides + Acetic Anhydride

Started by pHarmacist, October 06, 2003, 05:59:00 AM

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pHarmacist

Palladium-Catalyzed Reaction of Aryl Iodides with Acetic Anhydride. A Carbon Monoxide-Free Synthesis of Acetophenones
Sandro Cacchi,* Giancarlo Fabrizi, Federica Gavazza, and Antonella Goggiamani

Org. Lett., 5 (3), 289 -291, 2003

(http://pharmacist.the-hive.tripod.com/acetophen.pdf)
DOI:

10.1021/ol027243b S1523-7060(02)07243-7



https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000462963-file_h4ro.gif" title="View this image">


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.


Rhodium

Nifty, buy does it really offer any significant advantages over Friedel-Crafts acylation (using Polyphosphoric acid and GAA)?

pHarmacist

Not really, but it's just another possibility...