Issue 9, 2022

Electrophilic hydrophosphonylation of aldimines with alkylphosphonochloridates provides access to (E)-alk-1-enylphosphonamidates

Abstract

Various α,β-unsaturated (E)-alkenylphosphonamidates were prepared in excellent stereo- and regioselectivities via the electrophilic hydrophosphonylation of cyclic and acyclic aldimines with alkylphosphonochloridates in the presence of base. For unsaturated aldimines, only their respective imine bonds were hydrophosphonylated regiospecifically. The reaction provided a new strategy for the synthesis of (E)-alk-1-enylphosphonamidates via a tandem phosphorylation, deprotonation, and intramolecular 1,5-hydride transfer sequence process from readily available aldimine and alkylphosphonochloridate starting materials. The strategy established the first one-pot electrophilic rather than nucleophilic hydrophosphonylation of aldimines without external hydride donors.

Graphical abstract: Electrophilic hydrophosphonylation of aldimines with alkylphosphonochloridates provides access to (E)-alk-1-enylphosphonamidates

Supplementary files

Article information

Article type
Research Article
Submitted
31 Dec 2021
Accepted
12 Mar 2022
First published
14 Mar 2022

Org. Chem. Front., 2022,9, 2464-2470

Electrophilic hydrophosphonylation of aldimines with alkylphosphonochloridates provides access to (E)-alk-1-enylphosphonamidates

Z. Fu, Y. Lei, F. Sun and J. Xu, Org. Chem. Front., 2022, 9, 2464 DOI: 10.1039/D1QO01949J

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