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Hydrazone Phosphaketene as a Synthetic Platform To Obtain Three Classes of 1,2,4-Diazaphosphol Derivatives by Switchable Chemoselectivity Strategies

Authors :
Wang, Xin
Chen, Dong-Ping
Wang, Wen-Peng
Yang, Chun-Hong
Li, Ming
Xu, Wen-Bo
Wang, Xi-Cun
Quan, Zheng-Jun
Source :
Organic Letters; May 2024, Vol. 26 Issue: 17 p3575-3580, 6p
Publication Year :
2024

Abstract

We introduce switchable chemoselectivity strategies based on the hydrazone phosphaketene intermediate to synthesize three classes of 1,2,4-diazaphosphol derivatives. First, the five-membered heterocyclic P and O anion intermediates acted as nucleophilic agents in the selective construction of C–P and C–O bonds. Second, the phosphinidene served as a phosphorus synthon, allowing for the formation of C–P and C–N bonds. Finally, a stepwise mechanism, supported by DFT calculations, was invoked to explain the reaction selectivity.

Details

Language :
English
ISSN :
15237060 and 15237052
Volume :
26
Issue :
17
Database :
Supplemental Index
Journal :
Organic Letters
Publication Type :
Periodical
Accession number :
ejs67017098
Full Text :
https://doi.org/10.1021/acs.orglett.4c00993