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Insight into the Mechanism of the Acylation of Alcohols with Acid Anhydrides Catalyzed by Phosphoric Acid Derivatives

Hiroyuki Hayashi, Shotaro Yasukochi, Tatsuhiro Sakamoto, Manabu Hatano* and Kazuaki Ishihara*

*Kobe Pharmaceutical University, Kobe 658-8558; Nagoya University, Nagoya 464-8603, Japan, Email: mhatanokobepharma-u.ac.jp, ishiharacc.nagoya-u.ac.jp

H. Hayashi, S. Yasukochi, T. Sakamoto, M. Hatano, K. Ishihara, J. Org. Chem., 2021, 86, 5197-5212.

DOI: 10.1021/acs.joc.1c00102 (free Supporting Information)


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Abstract

Inexpensive phosphoric acid (H3PO4) catalyzes a safe and simple acylation of alcohols with acid anhydrides. In situ-generated diacylated mixed anhydrides are proposed as the active species - acting as efficient catalytic acyl transfer reagents. A 23 g scale synthesis of an ester was demonstrated.

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proposed mechanism



Key Words

acylation, acetic acid esters, pivalic acid esters


ID: J42-Y2021