Literature DB >> 19956351

Nucleophilic difluoromethylation and difluoromethylenation of aldehydes and ketones using diethyl difluoromethylphosphonate.

Petr Beier1, Anastasia V Alexandrova, Mikhail Zibinsky, G K Surya Prakash.   

Abstract

New methodology for difluoromethylation and difluoromethylenation of aldehydes and ketones based on nucleophilic fluorination using diethyl difluoromethylphosphonate (1) was developed.

Entities:  

Year:  2008        PMID： 19956351      PMCID： PMC2632590          DOI： 10.1016/j.tet.2008.10.006

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  20 in total

1.  Perfluoroalkylation with Organosilicon Reagents.

Authors:  G. K. Surya Prakash; Andrei K. Yudin
Journal:  Chem Rev       Date:  1997-05-08       Impact factor: 60.622

Review 2.  Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.

Authors:  Jun-An Ma; Dominique Cahard
Journal:  Chem Rev       Date:  2004-12       Impact factor: 60.622

Review 3.  Fluorinated phosphonates: synthesis and biomedical application.

Authors:  Vadim D Romanenko; Valery P Kukhar
Journal:  Chem Rev       Date:  2006-09       Impact factor: 60.622

4.  A remarkably efficient fluoroalkylation of cyclic sulfates and sulfamidates with PhSO2CF2H: facile entry into beta-difluoromethylated or beta-difluoromethylenated alcohols and amines.

Authors:  Chuanfa Ni; Jun Liu; Laijun Zhang; Jinbo Hu
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Synthesis and transformation of [difluoro(phenylseleno)methyl]- trimethylsilane.

Authors:  Ying-Ying Qin; Xiao-Long Qiu; Yan-Yan Yang; Wei-Dong Meng; Feng-Ling Qing
Journal:  J Org Chem       Date:  2005-10-28       Impact factor: 4.354

6.  Radical (phenylsulfonyl)difluoromethylation with iododifluoromethyl phenyl sulfone.

Authors:  Ya Li; Jun Liu; Laijun Zhang; Lingui Zhu; Jinbo Hu
Journal:  J Org Chem       Date:  2007-06-23       Impact factor: 4.354

7.  Preparation of tri- and difluoromethylsilanes via an unusual magnesium metal-mediated reductive tri- and difluoromethylation of chlorosilanes using tri- and difluoromethyl sulfides, sulfoxides, and sulfones.

Authors:  G K Surya Prakash; Jinbo Hu; George A Olah
Journal:  J Org Chem       Date:  2003-05-30       Impact factor: 4.354

8.  Difluoromethyl phenyl sulfone as a selective difluoromethylene dianion equivalent: one-pot stereoselective synthesis of anti-2,2-difluoropropane-1,3-diols.

Authors:  G K Surya Prakash; Jinbo Hu; Thomas Mathew; George A Olah
Journal:  Angew Chem Int Ed Engl       Date:  2003-11-03       Impact factor: 15.336

9.  New electrophilic difluoromethylating reagent.

Authors:  G K Surya Prakash; Csaba Weber; Sujith Chacko; George A Olah
Journal:  Org Lett       Date:  2007-04-20       Impact factor: 6.005

10.  Aspartyl phosphonates and phosphoramidates: the first synthetic inhibitors of bacterial aspartate-semialdehyde dehydrogenase.

Authors:  Russell J Cox; Jennifer S Gibson; María Belén Mayo Martín
Journal:  Chembiochem       Date:  2002-09-02       Impact factor: 3.164
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  3 in total

1.  Synthesis, Derivatization, and Structural Analysis of Phosphorylated Mono-, Di-, and Trifluorinated d-Gluco-heptuloses by Glucokinase: Tunable Phosphoglucomutase Inhibition.

Authors:  Jian-She Zhu; Kyle M Stiers; Sherany M Winter; Anthony D Garcia; Antoine F Versini; Lesa J Beamer; David L Jakeman
Journal:  ACS Omega       Date:  2019-04-18

2.  Highly Diastereoselective Construction of Carbon- Heteroatom Quaternary Stereogenic Centers in the Synthesis of Analogs of Bioactive Compounds: From Monofluorinated Epoxyalkylphosphonates to α-Fluoro-, β-, or γ-Amino Alcohol Derivatives of Alkylphosphonates.

Authors:  Magdalena Rapp; Klaudia Margas-Musielak; Patrycja Kaczmarek; Agnieszka Witkowska; Tomasz Cytlak; Tomasz Siodła; Henryk Koroniak
Journal:  Front Chem       Date:  2021-06-02       Impact factor: 5.221

3.  Efficient Difluoromethylation of sp(3) Carbon Nucleophiles by Bromodifluoromethylation Reagents with Organic Bases.

Authors:  Guokai Liu; Xin Wang; Xu Lu; Xiu-Hua Xu; Etsuko Tokunaga; Norio Shibata
Journal:  ChemistryOpen       Date:  2012-10-11       Impact factor: 2.911
  3 in total

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