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Oxidative Debenzylation of N-Benzyl Amides and O-Benzyl Ethers Using Alkali Metal Bromide

Katsuhiko Moriyama*, Yu Nakamura and Hideo Togo*

*Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan, Email: moriyamafaculty.chiba-u.jp, togofaculty.chiba-u.jp

K. Moriyama, Y. Nakamura, H. Togo, Org. Lett., 2014, 16, 3812-3815.

DOI: 10.1021/ol501703y  (free Supporting Information)


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Abstract

Formation of a bromo radical through the oxidation of bromide under mild conditions enables an oxidative debenzylation of N-benzyl amides and O-benzyl ethers to provide the corresponding amides and carbonyl compounds in high yields.


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Key Words

debenzylation (amides, alcohols), oxone, ketones


ID: J54-Y2014