Blue-light assisted transformation of C[double bond, length as m-dash]S and P[double bond, length as m-dash]S bonds of thioamides and thiophosphonyl diamides into C[double bond, length as m-dash]N and P[double bond, length as m-dash]N bonds of N-sulfonyl amidines via interaction with iminoiodinanes

Abstract

Photochemical and photocatalytic reactions of thioamides and thiophosphonyl diamides with iminoiodinanes have been developed. Blue-light promoted interaction of aromatic, aliphatic, and heterocyclic thioamides with iminoiodinane PhINTs furnished the corresponding N-sulfonyl amidines in 47–87% yields. A photocatalytic transformation of thiophosphonyl diamides in the presence of iminoiodinane PhINTs, catalyzed by Ru(bpy)3Cl2, was found to provide a route to phosphorus-containing N-sulfonyl amidines in 49–67% yields.

Graphical abstract: Blue-light assisted transformation of C [[double bond, length as m-dash]] S and P [[double bond, length as m-dash]] S bonds of thioamides and thiophosphonyl diamides into C [[double bond, length as m-dash]] N and P [[double bond, length as m-dash]] N bonds of N-sulfonyl amidines via interaction with iminoiodinanes

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Article information

Article type
Paper
Submitted
30 Sep 2025
Accepted
15 Nov 2025
First published
29 Nov 2025

New J. Chem., 2025, Advance Article

Blue-light assisted transformation of C[double bond, length as m-dash]S and P[double bond, length as m-dash]S bonds of thioamides and thiophosphonyl diamides into C[double bond, length as m-dash]N and P[double bond, length as m-dash]N bonds of N-sulfonyl amidines via interaction with iminoiodinanes

V. G. Ilkin, P. S. Silaichev, V. O. Filimonov, A. V. Nikulin, N. A. Beliaev, T. V. Beryozkina, P. A. Slepukhin, W. Dehaen and V. A. Bakulev, New J. Chem., 2025, Advance Article , DOI: 10.1039/D5NJ03889H

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