[PDF] Atherton–Todd reaction: mechanism, scope and applications | Semantic Scholar (2024)

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@article{Lecorre2014AthertonToddRM, title={Atherton–Todd reaction: mechanism, scope and applications}, author={St{\'e}phanie Le corre and Mathieu Berchel and H{\'e}l{\`e}ne Couthon-Gourv{\`e}s and Jan Haelters and Paul-Alain Jaffr{\`e}s}, journal={Beilstein Journal of Organic Chemistry}, year={2014}, volume={10}, pages={1166 - 1196}, url={https://api.semanticscholar.org/CorpusID:11488829}}
  • S. Le corre, M. Berchel, P. Jaffrès
  • Published in Beilstein Journal of Organic… 21 May 2014
  • Chemistry

The activation of a phenol group as a phosphate which allows for subsequent transformations such as cross coupling and reduction and the use of the AT reaction for the production of compounds employed for biological applications is investigated.

123 Citations

Background Citations

3

Methods Citations

1

Results Citations

1

123 Citations

Study on the Atherton–Todd reaction mechanism
    V. MitovaN. KosevaK. Troev

    Chemistry

  • 2014

A new mechanism of the Atherton–Todd reaction is discussed. The first step of the reaction between diesters of H-phosphonic acid and carbon tetrachloride in the presence of a base, commonly

Experimental study on the microreactor-assisted synthesis of phosphinic chlorides with varying steric hindrance
    A. JasiakKrzysztof OwsianikBartłomiej GostyńskiG. MielniczakC. StevensJ. Drabowicz

    Chemistry

  • 2020

An efficient and catalyst-free method for the preparation of optically active and racemic mono-substituted t-butyl phosphinic chlorides tBuRP(O)Cl under flow conditions was reported. A variety of

  • PDF
Reactivity of P–H Group of H-Phosphinic Acid and Its Derivatives
    K. Troev

    Chemistry

  • 2018
Reinvestigation of the iodine-mediated phosphoramidation reaction of amines and P(OR)3 and its synthetic applications.
    Xunwei ChenZecai XiaoHan-Yang ChuBo-Chi WangA. Peng

    Chemistry

  • 2018

Investigation of the iodine-mediated phosphoramidation reaction of amines and trialkyl phosphites shows that this underused method is actually a mild, practical and general way to synthesizeosphoramidates and will have wide applications.

  • 10
Evaluation and Development of Methodologies for the Synthesis of Thiophosphinic Acids.
    Karen R. WintersJean-Luc Montchamp

    Chemistry

    The Journal of organic chemistry

  • 2020

Two major approaches were selected: the Stec reaction of phosphorus amides with carbon disulfide; and the one-pot synthesis of thiophosphorus acids from H-phosphinates, an organometallic nucleophile, and quenching with elemental sulfur.

  • 3
  • PDF
Synthesis and Characterization of Alkoxy Spirophosphoranes Prepared from Hydrospirophosphoranes and Sodium Alcoholates
    Wang DaiQiangqiang Liu S. Cao

    Chemistry

  • 2016

The Atherton–Todd-type reaction of hydrospirophosphoranes (HSPs) and sodium alcoholates was investigated. Direct alkoxylation of HSPs was accomplished with sodium alcoholates in acetonitrile under

  • 9
Copper-Catalyzed Phosphorylation of N,N-Disubstituted Hydrazines: Synthesis of Multisubstituted Phosphorylhydrazides as Potential Anticancer Agents.
    Lvyin ZhengLiuhuan Cai Wei Guo

    Chemistry, Medicine

    The Journal of organic chemistry

  • 2022

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.

  • 7
Diselenide-Mediated Catalytic Functionalization of Hydrophosphoryl Compounds.
    HandokoZacharia BenslimaneP. Arora

    Chemistry

    Organic letters

  • 2020

A diaryldiselenide catalyst for cross-dehydrogenative nucleophilic functionalization of hydrophosphoryl compounds and phosphorus and selenium NMR studies reveal the existence of a P-Se bond intermediate, and structural analyses indicate a stereospecific reaction.

  • 26
Copper catalyzed tandem Chan–Lam type C—N and Staudinger-phosphite N—P coupling for the synthesis of N-arylphosphoramidates
    N. A. DangrooTabassum AraB. DarMohmmed A Khuroo

    Chemistry

    Catalysis Communications

  • 2019
  • 10
Practical Synthesis of Phosphinic Amides/Phosphoramidates via Catalytic Oxidative Coupling of Amines and P(O)-H Compounds.
    Chen TanXinyuan Liu Jiajing Tan

    Chemistry

    Chemistry

  • 2019

This operationally simple protocol provides unprecedented generic access to phosphinic amides/phosphoramidate derivatives in good yields and short reaction time and is applicable to scale-up syntheses as well as late stage functionalization of drug molecules.

  • 27

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178 References

Systematic study for the stereochemistry of the Atherton–Todd reaction
    Biquan XiongYongbo ZhouChangqiu ZhaoM. GotoS. YinLi‐Biao Han

    Chemistry

  • 2013
  • 46
Phosphorylation of Amino(aryl)methylphosphonates by the Atherton—Todd Reaction
    L. MinaevaL. S. PatrikeevaM. KabachnikI. Beletskaya

    Chemistry

  • 2010

We were the first to perform phosphorylation of amino(aryl)methylphosphonates having a primary amino group under the Atherton–Todd reaction conditions. The reactions of amino(aryl)methylphosphonates

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Synthesis of new organophosphorus compounds using the atherton–todd reaction as a versatile tool
    S. WagnerM. RakotomalalaYana BykovO. WalterM. Döring

    Chemistry

  • 2012

This article discusses the behavior of seven organophosphorus compounds under Atherton–Todd conditions. Therefore, the reactivity and selectivity of different (phen)oxaphosphinines,

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Chemistry of Trichlorosilyl Enolates. 1. New Reagents for Catalytic, Asymmetric Aldol Additions
    S. DenmarkS. B. WinterXiping SuKen‐Tsung Wong

    Chemistry

  • 1996

The asymmetric aldol addition is among the most powerful reactions in synthetic organic chemistry and has been extensively studied over the past 15 years.1 The strategies for reagentcontrolled

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Unexpected insertion of CO2 into the pentacoordinate P-N bond: Atherton-Todd-type reaction of hydrospirophosphorane with amines.
    S. CaoP. Gao Yufen Zhao

    Chemistry

    The Journal of organic chemistry

  • 2013

The Atherton-Todd-type reaction of pentacoordinate hydrospirophosphoranes with amines was investigated, and a novel CO2 insertion reaction into the pentacoordinate P-N bond under mild conditions was

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Investigations of the nucleophilic displacement at the tetrahedral phosphorus - kinetic effects of the nucleophile for a given stereochemistry
    R. CorriuG. LanneauD. Leclercq

    Chemistry

  • 1986
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Synthesis of nonsymmetrical dialkylamines on the basis of diphenylphosphinic amides
    N. BondarenkoA. KharlamovA. G. Vendilo

    Chemistry

  • 2009

A facile method for the synthesis of nonsymmetrical dialkylamines (CnH2n+1)2NH (n = 1–12) using the Ph2P(O) protecting group was developed. The method includes successive transformation of

  • 13
Phosphoramidates: Features of the formation mechanism and the relationship structure-bioaction
    V. KrutikovA. V. ErkinV. V. Krutikova

    Chemistry

    Russian Journal of General Chemistry

  • 2012

Mechanism of the synthesis of phosphoramidates by Todd-Atherton reaction is based on the primary interaction of a polyhaloalkane with the highly basic amine to form a 1:1 associate. The subsequent

  • 9
Synthesis of Phosphoramides for the Lewis Base-Catalyzed Allylation and Aldol Addition Reactions.
    S. DenmarkXiping Su Jun Young Choi

    Chemistry

    The Journal of organic chemistry

  • 1999

Both chiral and achiral phosphoramides of diverse structure were prepared from diamines by the coupling to phosphorus(V) or phosphorus(III) reagents. Several enantiopure

  • 68
Mild and nonracemizing conditions for Ullmann-type diaryl ether formation between aryl iodides and tyrosine derivatives.
    Q. CaiGang HeD. Ma

    Chemistry

    The Journal of organic chemistry

  • 2006

Short protocols for assembling (S,S)-isodityrosine and K-13 are developed on the basis of studies on coupling reaction of L-tyrosine derivatives and L-phenylalanine-derived iodides and reaction yields are moderate.

  • 68

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