Literature DB >> 23734560

One-pot synthesis of hypervalent iodine reagents for electrophilic trifluoromethylation.

Václav Matoušek1, Ewa Pietrasiak, Rino Schwenk, Antonio Togni.   

Abstract

Simplified syntheses suited for large scale preparations of the two hypervalent iodine reagents 1 and 2 for electrophilic trifluoromethylation are reported. In both cases, the stoichiometric oxidants sodium metaperiodate and tert-butyl hypochlorite have been replaced by trichloroisocyanuric acid. Reagent 1 is accessible in a one-pot procedure from 2-iodobenzoic acid in 72% yield. Reagent 2 was prepared via fluoroiodane 11 in a considerably shorter reaction time and with no need of an accurate temperature control.

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Year:  2013        PMID: 23734560     DOI: 10.1021/jo400774u

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  17 in total

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2.  Efficient Synthesis of β-CF3/SCF3-Substituted Carbonyls via Copper-Catalyzed Electrophilic Ring-Opening Cross-Coupling of Cyclopropanols.

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Journal:  Org Lett       Date:  2015-04-17       Impact factor: 6.072

3.  Expanding the Scope of 2'-SCF3 Modified RNA.

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4.  Mild silver-mediated geminal difluorination of styrenes using an air- and moisture-stable fluoroiodane reagent.

Authors:  Nadia O Ilchenko; Boris O A Tasch; Kálmán J Szabó
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-21       Impact factor: 15.336

5.  Catalytic Intramolecular Aminofluorination, Oxyfluorination, and Carbofluorination with a Stable and Versatile Hypervalent Fluoroiodine Reagent.

Authors:  Weiming Yuan; Kálmán J Szabó
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-09       Impact factor: 15.336

6.  Synthesis, characterization and initial evaluation of 5-nitro-1-(trifluoromethyl)-3H-1λ(3),2-benziodaoxol-3-one.

Authors:  Nico Santschi; Roman C Sarott; Elisabeth Otth; Reinhard Kissner; Antonio Togni
Journal:  Beilstein J Org Chem       Date:  2014-01-02       Impact factor: 2.883

7.  Product Control in Alkene Trifluoromethylation: Hydrotrifluoromethylation, Vinylic Trifluoromethylation, and Iodotrifluoromethylation using Togni Reagent.

Authors:  Hiromichi Egami; Yoshihiko Usui; Shintaro Kawamura; Sayoko Nagashima; Mikiko Sodeoka
Journal:  Chem Asian J       Date:  2015-06-16

8.  Access to a new class of synthetic building blocks via trifluoromethoxylation of pyridines and pyrimidines.

Authors:  Pengju Feng; Katarzyna N Lee; Johnny W Lee; Chengbo Zhan; Ming-Yu Ngai
Journal:  Chem Sci       Date:  2015-10-07       Impact factor: 9.825

9.  Isolation and Reactivity of Trifluoromethyl Iodonium Salts.

Authors:  Johnathan N Brantley; Andrew V Samant; F Dean Toste
Journal:  ACS Cent Sci       Date:  2016-05-13       Impact factor: 14.553

10.  Rhodium-Catalyzed Geminal Oxyfluorination and Oxytrifluoro-Methylation of Diazocarbonyl Compounds.

Authors:  Weiming Yuan; Lars Eriksson; Kálmán J Szabó
Journal:  Angew Chem Int Ed Engl       Date:  2016-05-24       Impact factor: 15.336

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