Direct Synthesis of ortho-Halogenated Arylphosphonates via a Three-Component Reaction Involving Arynes DOI

Yuanting Huang,

Y. Hu,

Yukun Han

и другие.

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(9), С. 7010 - 7018

Опубликована: Апрель 21, 2021

A three-component reaction involving arynes, trialkyl phosphites, and halides has been achieved under mild conditions. This transformation provides a direct synthetic approach to ortho-halogenated arylphosphonates, which could be rapidly converted diversely ortho-functionalized arylphosphorus compounds.

Язык: Английский

Direct visible-light-induced synthesis of P-stereogenic phosphine oxides under air conditions DOI Creative Commons
Ying Zhang, Yuan Jia, Guanglong Huang

и другие.

Chemical Science, Год журнала: 2022, Номер 13(22), С. 6519 - 6524

Опубликована: Янв. 1, 2022

We describe a simple and efficient visible-light-induced C–P bond forming reaction for the synthesis of P-chiral heteroaryl phosphine oxides in moderate to high yields with excellent ee values (97–99% ee).

Язык: Английский

Процитировано

18

Primary Amination of Ar2P(O)–H with (NH4)2CO3 as an Ammonia Source under Simple and Mild Conditions and Its Extension to the Construction of Various P–N or P–O Bonds DOI
Yushi Tan, Yaping Han, Yuecheng Zhang

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(5), С. 3254 - 3264

Опубликована: Янв. 24, 2022

A facile and efficient method for the synthesis of primary phosphinamides from Ar2P(O)-H reagents with stable readily available ammonium carbonate as an ammonia source is disclosed herein first time. This ethyl bromoacetate-mediated amination proceeds smoothly under mild simple conditions, without any metal catalyst or oxidant. Moreover, this also appropriate reaction a variety amines, alcohols, phenols to construct P-N P-O bonds, features handy operation, good functional group tolerance, broad substrate scope.

Язык: Английский

Процитировано

17

Progress in phosphorylation of natural products DOI

Xiaoran Mao,

Jiaqi Chen,

Yingrui Yao

и другие.

Molecular Biology Reports, Год журнала: 2024, Номер 51(1)

Опубликована: Май 27, 2024

Язык: Английский

Процитировано

4

CuH-Catalyzed Reductive Coupling of Nitroarenes with Phosphine Oxides for the Direct Synthesis of Phosphamides DOI

Jie Tang,

Zhiyou Li, Qi Meng

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7848 - 7858

Опубликована: Май 29, 2024

A CuH-catalyzed reductive coupling of nitroarenes with phosphine oxides is developed, which produces a series phosphamides in moderate to excellent yields good functional group tolerance. Gram-scale synthesis and late-stage modification nitro-aromatic molecule niclosamide are also successfully conducted. The mechanism study shows that the nitro transformed after being reduced nitroso nucleophilic addition procedure involved during reaction.

Язык: Английский

Процитировано

4

Opening up the Toolbox: Synthesis and Mechanisms of Phosphoramidates DOI Creative Commons
Emeka J. Itumoh,

Shailja Data,

Erin M. Leitao

и другие.

Molecules, Год журнала: 2020, Номер 25(16), С. 3684 - 3684

Опубликована: Авг. 13, 2020

This review covers the main synthetic routes to and corresponding mechanisms of phosphoramidate formation. The can be separated into six categories: salt elimination, oxidative cross-coupling, azide, reduction, hydrophosphinylation, phosphoramidate-aldehyde-dienophile (PAD). Examples some important compounds synthesized through these are provided. As an class organophosphorus compounds, applications also briefly introduced.

Язык: Английский

Процитировано

24

Copper-Catalyzed Phosphorylation of N,N-Disubstituted Hydrazines: Synthesis of Multisubstituted Phosphorylhydrazides as Potential Anticancer Agents DOI
Lvyin Zheng,

Liuhuan Cai,

Weijie Mei

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(9), С. 6224 - 6236

Опубликована: Апрель 20, 2022

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 proceeds under mild conditions without addition any external oxidants bases. This work reported here represents a direct P(═O)-N-N bond formation with advantages being operationally simple, good functional group tolerance, high atom step economy. Furthermore, selected exhibit potential inhibitory activity against tumor cells, which can be used in field screening anticancer agents as new chemical entities.

Язык: Английский

Процитировано

15

Metal-Free Regioselective Hydrophosphorodithioation of Spirovinylcyclopropyl Oxindoles: Rapid Access to Allyl Dialkylphosphorodithioates DOI
Jiahua Wang, Fang Han, Siyuan Hao

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(19), С. 12844 - 12853

Опубликована: Сен. 27, 2022

Phosphorodithioates are important substructures due to their great use in bioactive compounds and functional materials. A metal-free 1,5-addition of spirovinylcyclopropyl oxindoles have been developed by choosing P4S10 alcohol as nucleophiles through the regioselective ring-opening oxindoles. This method provides access allylic organothiophosphates with high efficiency, wide group tolerance, good chemo- regioselectivity, E-selectivity. 1,3-Addition products were also prepared yield. Furthermore, resulting could be readily transformed into other derivatives.

Язык: Английский

Процитировано

15

NaOAc-Assisted Aerobic Oxidation Protocol for the Synthesis of Pentacoordinate Chalcogenyl Spirophosphoranes with P–Se/P–S Bonds under Open Air DOI
Yang Zhang, Yanchun Guo, Yufen Zhao

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(5), С. 3259 - 3270

Опубликована: Фев. 21, 2024

The NaOAc-assisted aerobic oxidation reaction of pentacoordinate hydrospirophosphoranes and dichalcogenyl compounds with open air as a green oxidant has been developed under mild conditions. A series novel spirophosphoranes P–Se/P–S bonds were synthesized in excellent yields. mechanism was determined by 31P nuclear magnetic resonance tracing experiments, high-resolution mass spectrometry X-ray diffraction analysis. method features broad substrate scope, good functional group tolerance, high degree atomic utilization is meaningful for the synthesis bioactive chalcogenphosphate chalcogen phosphorus moieties.

Язык: Английский

Процитировано

3

Photocatalyzed Aerobic Cross-Dehydrogenative Coupling of Diarylphosphine Oxides with Alcohols and Phenols DOI
Hongyan Zhou,

Chengqi Wu,

Yating Han

и другие.

Organic Letters, Год журнала: 2024, Номер 26(12), С. 2435 - 2439

Опубликована: Март 19, 2024

A photocatalytic cross-dehydrogenative coupling of diarylphosphine oxides with alcohols and phenols has been developed. Using organic dye Rose Bengal as the photocatalyst air oxidant, reaction proceeded smoothly at room temperature. Both were feasible, affording various organophosphinates in high yields. The absence a halogenating reagent, transition-metal catalyst, green mild conditions make this strategy environmentally benign sustainable. Mechanistic studies indicated that is enabled by cooperation photoredox catalysis photosensitization.

Язык: Английский

Процитировано

3

Concept and Evolution of the Atherton-Todd Reaction DOI

Siqiang Fang,

Zanjiao Liu,

Zhishan Su

и другие.

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 9660 - 9671

Опубликована: Май 22, 2025

Язык: Английский

Процитировано

0