Synlett 2025; 36(05): 474-479
DOI: 10.1055/s-0043-1775388
letter

Direct Synthesis of N-Substituted Phosphinecarboxamides from [TBA][P(SiCl3)2] and Isonitriles

Bo Yang
,
Xin Wang
,
Yao Chai
,
Wen-Bo Xu
,
Ya-Ling Tian
,
Yong-Jun Ma
,
Anwar I. Alduma
,
Xin-Rui Cao
,
Xi-Cun Wang
,
Dong-Ping Chen
,
Zheng-Jun Quan
We thank the National Natural Science Foundation of China (Nos. 22061038, 22067018 and 21562036) for financial support.


Abstract

In this investigation, N-substituted phosphinecarboxamides were produced through the reaction of [TBA][P(SiCl3)2] with isonitriles. This method capitalizes on the flexibility of isonitriles as a source of both nitrogen and carbonyl groups, offering a novel route to the generation of PH2-type compounds. This approach is characterized by rapid reaction times, simple procedural requirements, compatibility with a diverse array of substrates, and the conversion of [TBA][P(SiCl3)2] into organic phosphorus compounds. Additionally, we systematically studied the reaction mechanism of isonitrile with [TBA][P(SiCl3)2] through controlled experiments and density functional theory (DFT) calculations.

Supporting Information



Publikationsverlauf

Eingereicht: 11. Juni 2024

Angenommen nach Revision: 15. Juli 2024

Artikel online veröffentlicht:
29. August 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany