Literature DB >> 28535057

Trifluoromethylation of Secondary Nitroalkanes.

Amber A S Gietter-Burch1, Vijayarajan Devannah1, Donald A Watson1.   

Abstract

Using a commercially available Umemoto's reagent, the metal-free trifluoromethylation of nitroalkanes is now possible. This method provides a general, high-yielding synthesis of α-(trifluoromethyl)nitroalkanes. The quaternary α-(trifluoromethyl)nitroalkanes obtained from this transformation can be elaborated to a variety of complex nitrogen-containing molecules, including α-(trifluoromethyl)amines.

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Year:  2017        PMID： 28535057      PMCID： PMC5531277          DOI： 10.1021/acs.orglett.7b01196

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  34 in total

1.  Mild electrophilic trifluoromethylation of carbon- and sulfur-centered nucleophiles by a hypervalent iodine(III)-CF3 reagent.

Authors:  Iris Kieltsch; Patrick Eisenberger; Antonio Togni
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

2.  Discovery of 1-amino-5H-pyrido[4,3-b]indol-4-carboxamide inhibitors of Janus kinase 2 (JAK2) for the treatment of myeloproliferative disorders.

Authors:  Jongwon Lim; Brandon Taoka; Ryan D Otte; Kerrie Spencer; Christopher J Dinsmore; Michael D Altman; Grace Chan; Craig Rosenstein; Sujata Sharma; Hua-Poo Su; Alexander A Szewczak; Lin Xu; Hong Yin; Joan Zugay-Murphy; C Gary Marshall; Jonathan R Young
Journal:  J Med Chem       Date:  2011-09-26       Impact factor: 7.446

3.  Palladium catalyzed vinyltrifluoromethylation of aryl halides through decarboxylative cross-coupling with 2-(trifluoromethyl)acrylic acid.

Authors:  Subban Kathiravan; Ian A Nicholls
Journal:  Org Lett       Date:  2015-03-31       Impact factor: 6.005

4.  (Z)- or (E)-Selective hydrogenation of potassium (3,3,3-trifluoroprop-1-yn-1-yl)trifluoroborate: route to either isomer of β-trifluoromethylstyrenes.

Authors:  P Veeraraghavan Ramachandran; Wataru Mitsuhashi
Journal:  Org Lett       Date:  2015-02-23       Impact factor: 6.005

5.  Benzylation of nitroalkanes using copper-catalyzed thermal redox catalysis: toward the facile C-alkylation of nitroalkanes.

Authors:  Peter G Gildner; Amber A S Gietter; Di Cui; Donald A Watson
Journal:  J Am Chem Soc       Date:  2012-06-12       Impact factor: 15.419

Review 6.  CF(3)-bearing aromatic and heterocyclic building blocks.

Authors:  Manfred Schlosser
Journal:  Angew Chem Int Ed Engl       Date:  2006-08-18       Impact factor: 15.336

7.  Rapid decarboxylative allylation of nitroalkanes.

Authors:  Alexander J Grenning; Jon A Tunge
Journal:  Org Lett       Date:  2010-02-19       Impact factor: 6.005

8.  Highly Diastereoselective Michael Reactions Using β-Nitrocarbonyl Nucleophiles.

Authors:  Amber A S Gietter-Burch; Roxana E Mitrut; Donald A Watson
Journal:  Org Lett       Date:  2015-10-26       Impact factor: 6.005

9.  A one-pot amidation of primary nitroalkanes.

Authors:  Kenneth E Schwieter; Jeffrey N Johnston
Journal:  Chem Commun (Camb)       Date:  2016-01-04       Impact factor: 6.222

10.  Organocatalytic enantioselective synthesis of 2,3-allenoates by intermolecular addition of nitroalkanes to activated enynes.

Authors:  Hui Qian; Xiuzhao Yu; Junliang Zhang; Jianwei Sun
Journal:  J Am Chem Soc       Date:  2013-11-21       Impact factor: 15.419
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  3 in total

1.  Nickel-Catalyzed Asymmetric C-Alkylation of Nitroalkanes: Synthesis of Enantioenriched β-Nitroamides.

Authors:  Vijayarajan Devannah; Rajgopal Sharma; Donald A Watson
Journal:  J Am Chem Soc       Date:  2019-05-17       Impact factor: 15.419

2.  Synthesis and applications of S-(trifluoromethyl)-2,8-bis(trifluoromethoxy)dibenzothiophenium triflate (Umemoto reagent IV).

Authors:  Sagar R Mudshinge; Gerald B Hammond; Teruo Umemoto
Journal:  J Fluor Chem       Date:  2022-07-03       Impact factor: 2.226

3.  Leveraging Electron-Deficient Iminium Intermediates in a General Synthesis of Valuable Amines.

Authors:  Che-Sheng Hsu; Carlos R Gonçalves; Veronica Tona; Amandine Pons; Marcel Kaiser; Nuno Maulide
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-16       Impact factor: 16.823
  3 in total

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