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Copper-Catalyzed Phosphorylation of <i>N</i>,<i>N</i>-Disubstituted Hydrazines: Synthesis of Multisubstituted Phosphorylhydrazides as Potential Anticancer Agents

Lvyin Zheng, Liuhuan Cai, Weijie Mei, Gongping Liu, Ling Deng, Xiaoying Zou, Xiaoya Zhuo, Yumei Zhong, Wei Guo

2022The Journal of Organic Chemistry20 citationsDOI

Abstract

An efficient copper-catalyzed aerobic oxidative cross-dehydrogenative coupling reaction for the synthesis of multisubstituted phosphorylhydrazides from N,N-disubstituted hydrazines and hydrogen phosphoryl compounds is accomplished. The reaction proceeds under mild conditions without the addition of any external oxidants and bases. This work reported here represents a direct P(═O)–N–N bond formation with the advantages of being operationally simple, good functional group tolerance, and high atom and step economy. Furthermore, the selected compounds exhibit potential inhibitory activity against tumor cells, which can be used in the field of screening of anticancer agents as new chemical entities.

Topics & Concepts

ChemistryCatalysisAtom economyCombinatorial chemistryOxidative phosphorylationFunctional groupCopperReaction conditionsCoupling reactionOrganic chemistryBiochemistryPolymerCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques
Copper-Catalyzed Phosphorylation of <i>N</i>,<i>N</i>-Disubstituted Hydrazines: Synthesis of Multisubstituted Phosphorylhydrazides as Potential Anticancer Agents | Litcius