Literature DB >> 24839397

Trifluoromethylation of Heterocycles in Water at Room Temperature.

James C Fennewald1, Bruce H Lipshutz1.   

Abstract

Using a reaction medium containing nanoparticles consisting of commercially available TPGS-750-M in water, a combination of Langlois' reagent and t-BuOOH can be used to effect trifluoromethylation of several heterocyclic arrays, including heteroaromatics. These reactions take place at ambient temperatures, and the aqueous medium can be recycled.

Entities:  

Year:  2014        PMID： 24839397      PMCID： PMC4019426          DOI： 10.1039/C3GC42119H

Source DB:  PubMed          Journal:  Green Chem        ISSN： 1463-9262            Impact factor:   10.182


  21 in total

1.  Copper-mediated oxidative trifluoromethylation of boronic acids.

Authors:  Lingling Chu; Feng-Ling Qing
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

2.  Silver-mediated trifluoromethylation of arenes using TMSCF3.

Authors:  Yingda Ye; Shin Hee Lee; Melanie S Sanford
Journal:  Org Lett       Date:  2011-09-20       Impact factor: 6.005

3.  Heck couplings at room temperature in nanometer aqueous micelles.

Authors:  Bruce H Lipshutz; Benjamin R Taft
Journal:  Org Lett       Date:  2008-03-12       Impact factor: 6.005

4.  PQS: a new platform for micellar catalysis. RCM reactions in water, with catalyst recycling.

Authors:  Bruce H Lipshutz; Subir Ghorai
Journal:  Org Lett       Date:  2009-02-05       Impact factor: 6.005

5.  Direct cupration of fluoroform.

Authors:  Alessandro Zanardi; Maxim A Novikov; Eddy Martin; Jordi Benet-Buchholz; Vladimir V Grushin
Journal:  J Am Chem Soc       Date:  2011-12-02       Impact factor: 15.419

6.  TPGS-750-M: a second-generation amphiphile for metal-catalyzed cross-couplings in water at room temperature.

Authors:  Bruce H Lipshutz; Subir Ghorai; Alexander R Abela; Ralph Moser; Takashi Nishikata; Christophe Duplais; Arkady Krasovskiy; Ricky D Gaston; Robert C Gadwood
Journal:  J Org Chem       Date:  2011-05-09       Impact factor: 4.354

7.  Copper-catalyzed trifluoromethylation of aryl and vinyl boronic acids with an electrophilic trifluoromethylating reagent.

Authors:  Tianfei Liu; Qilong Shen
Journal:  Org Lett       Date:  2011-04-07       Impact factor: 6.005

8.  Palladium-catalyzed Suzuki-Miyaura coupling of pyridyl-2-boronic esters with aryl halides using highly active and air-stable phosphine chloride and oxide ligands.

Authors:  David X Yang; Steven L Colletti; Kevin Wu; Maoying Song; George Y Li; Hong C Shen
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

9.  Practical method for the Cu-mediated trifluoromethylation of arylboronic acids with CF3 radicals derived from NaSO2CF3 and tert-butyl hydroperoxide (TBHP).

Authors:  Yingda Ye; Stefan A Künzi; Melanie S Sanford
Journal:  Org Lett       Date:  2012-09-17       Impact factor: 6.005

10.  Synthesis of trifluoromethylated azines via nucleophilic oxidative substitution of hydrogen by trifluoromethyl carbanions.

Authors:  Rafał Loska; Monika Majcher; Mieczysław Makosza
Journal:  J Org Chem       Date:  2007-06-22       Impact factor: 4.354
View more
  9 in total

Review 1.  Mass Spectrometry-Based Protein Footprinting for Higher-Order Structure Analysis: Fundamentals and Applications.

Authors:  Xiaoran Roger Liu; Mengru Mira Zhang; Michael L Gross
Journal:  Chem Rev       Date:  2020-04-22       Impact factor: 60.622

2.  Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors:  Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal:  Chem Rev       Date:  2019-06-25       Impact factor: 60.622

3.  Copper(i) reagent-promoted hydroxytrifluoromethylation of enamides: flexible synthesis of substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one.

Authors:  Qing Wang; Peng Shi; Runsheng Zeng
Journal:  RSC Adv       Date:  2018-07-19       Impact factor: 4.036

4.  Transitioning organic synthesis from organic solvents to water. What's your E Factor?

Authors:  Bruce H Lipshutz; Subir Ghorai
Journal:  Green Chem       Date:  2014-08-01       Impact factor: 10.182

5.  Designer Micelles Accelerate Flux Through Engineered Metabolism in E. coli and Support Biocompatible Chemistry.

Authors:  Stephen Wallace; Emily P Balskus
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-08       Impact factor: 15.336

6.  Synthesis of 7-trifluoromethyl-7-deazapurine ribonucleoside analogs and their monophosphate prodrugs.

Authors:  Jong Hyun Cho; Leda C Bassit; Franck Amblard; Raymond F Schinazi
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2019-10-07       Impact factor: 1.381

7.  CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF3SO2Na.

Authors:  Hélène Guyon; Hélène Chachignon; Dominique Cahard
Journal:  Beilstein J Org Chem       Date:  2017-12-19       Impact factor: 2.883

8.  Synthesis of a 3'-C-ethynyl-β-d-ribofuranose purine nucleoside library: Discovery of C7-deazapurine analogs as potent antiproliferative nucleosides.

Authors:  Fabian Hulpia; Sam Noppen; Dominique Schols; Graciela Andrei; Robert Snoeck; Sandra Liekens; Peter Vervaeke; Serge Van Calenbergh
Journal:  Eur J Med Chem       Date:  2018-07-29       Impact factor: 6.514

9.  Direct C-H Trifluoromethylation of (Hetero)Arenes in Water Enabled by Organic Photoredox-Active Amphiphilic Nanoparticles.

Authors:  Fabian Eisenreich; Anja R A Palmans
Journal:  Chemistry       Date:  2022-07-28       Impact factor: 5.020
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.