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Reduction and Reductive Deuteration of Tertiary Amides Mediated by Sodium Dispersions with Distinct Proton Donor-Dependent Chemoselectivity

Bin Zhang, Hengzhao Li, Yuxuan Ding, Yuhao Yan and Jie An*

*College of Science, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China, Email: jie_ancau.edu.cn

B. Zhang, H. Li, Y. Ding, Y. Yan, J. An, J. Org. Chem., 2018, 83, 6006-6014.

DOI: 10.1021/acs.joc.8b00617 (free Supporting Information)


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Abstract

A practical and scalable single electron transfer reduction enables the reduction and reductive deuteration of tertiary amides in the presence of sodium dispersions. The chemoselectivity of this method highly depends on the nature of the proton donor. Whereas the combination of Na/EtOH affords alcohol products, the use of Na/NaOH/H2O leads to the formation of amines.

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Key Words

sodium, reduction of amides


ID: J42-Y2018