Journal of Organic Chemistry 2008-08-15

An efficient preparation of beta-aryl-beta-ketophosphonates by the TFAA/H3PO4-mediated acylation of arenes with phosphonoacetic acids.

George P Luke, Christopher K Seekamp, Zhe-Qing Wang, Bertrand L Chenard

Index: J. Org. Chem. 73(16) , 6397-6400, (2008)

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Abstract

Beta-aryl-beta-ketophosphonates can be efficiently prepared in good yield by using a TFAA/85% H 3PO 4-mediated acylation of electron-rich arenes with phosphonoacetic acids. The conditions offer advantages over existing methods of preparing these useful compounds by not requiring the use of strong base, cryogenics, or an anhydrous and inert atmosphere. Furthermore, some functional groups not tolerated with the reaction conditions used in existing methods are compatible with the herein described conditions.