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Sequential KOBu/FeCl3-catalyzed reductive phosphonylation of tertiary amides for the synthesis of α-amino phosphonates and phosphines. 2023

Yue Wang, and Xiaoyu Wu, and Liqun Yang, and Wei Liu, and Zhaoguo Zhang, and Xiaomin Xie
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. China. xiaominxie@sjtu.edu.cn.

A simple, mild and efficient sequential KOBu/FeCl3-catalyzed reductive phosphonylation of tertiary amides is herein described. This process first involved the KOBu-catalyzed selective semi-reduction of tertiary amides to hemiaminal intermediates by TMDS (1,1,3,3-tetramethyldisiloxane) and then the FeCl3-catalyzed nucleophilic addition of the hemiaminal intermediates to phosphonates, which allowed the straightforward synthesis of α-amino phosphonates in moderate to good yields. This method applied well to amides and lactams that bear no strong acidic α-hydrogens, and various functional groups, including methoxy, methylthio, cyano, halogen, and heterocycles, could be tolerated.

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