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Wet and Dry Processes for the Selective Transformation of Phosphonates to Phosphonic Acids Catalyzed by Brønsted Acids

Chunya Li, Yuta Saga, Shun-ya Onozawa, Shu Kobayashi, Kazuhiko Sato, Norihisa Fukaya and Li-Biao Han*

*National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki 305-8565, Japan, Email: libiao-hanaist.go.jp

C. Li, Y. Saga, S.-y. Onozawa, S. Kobayashi, K. Sato, N. Fukaya, L.-B. Han, J. Org. Chem., 2020, 85, 14411–14419.

DOI: 10.1021/acs.joc.0c00550 (free Supporting Information)



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Abstract

TfOH catalyzes wet and dry processes for converting phosphonate esters to phosphonic acids in good yields. Whereas in the presence of water, a range of alkyl-, alkenyl-, and aryl-substituted phosphonates can be hydrolyzed to the corresponding phosphonic acids at 140°C, the conversion of dibenzyl phosphonates to the corresponding phosphonic acids takes place smoothly at 80°C in toluene.

 
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Key Words

hydrolysis


ID: J42-Y2020