Literature DB >> 25271542

Selective perfluoro- and polyfluoroarylation of Meldrum's acid.

Sameera M Senaweera1, Jimmie D Weaver.   

Abstract

This work describes the facile and mono-selective per- and polyfluoroarylation of Meldrum's acid to generate a versatile synthon for highly fluorinated α-phenyl acetic acid derivatives, which provide straightforward access to fluorinated building blocks. The reaction takes place quickly, and most products were isolated without the need for chromatography. Importantly, this method provides an alternative strategy to access α-arylated Meldrum's acids, which avoids the need for aryl-Pb(IV) salts or diaryliodonium salts. Furthermore, we demonstrate the synthetic versatility and utility of the Meldrum's acid products by subjecting our products to several derivatizations of the Meldrum's acid products as well as photocatalytic hydrodefluorination.

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Year:  2014        PMID: 25271542     DOI: 10.1021/jo502075p

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


  11 in total

1.  Selective and Scalable Perfluoroarylation of Nitroalkanes.

Authors:  Jon I Day; Jimmie D Weaver
Journal:  J Org Chem       Date:  2017-06-09       Impact factor: 4.354

2.  Hydrogen Bond Directed Photocatalytic Hydrodefluorination: Overcoming Electronic Control.

Authors:  Mohammad B Khaled; Roukaya K El Mokadem; Jimmie D Weaver
Journal:  J Am Chem Soc       Date:  2017-09-08       Impact factor: 15.419

3.  Dual C-F, C-H Functionalization via Photocatalysis: Access to Multifluorinated Biaryls.

Authors:  Sameera Senaweera; Jimmie D Weaver
Journal:  J Am Chem Soc       Date:  2016-02-18       Impact factor: 15.419

4.  Polyfluoroarylation of oxazolones: access to non-natural fluorinated amino acids.

Authors:  Kip A Teegardin; Jimmie D Weaver
Journal:  Chem Commun (Camb)       Date:  2017-04-27       Impact factor: 6.222

5.  A Selective Single Step Amidation of Polyfluoroarenes.

Authors:  Alyssa M Noel; Matthew Hamilton; Brockton Keen; Megan Despain; Jon Day; Jimmie D Weaver
Journal:  J Fluor Chem       Date:  2021-05-30       Impact factor: 2.226

6.  Photocatalytic C-F Reduction and Functionalization.

Authors:  Sameera Senaweera; Jimmie D Weaver
Journal:  Aldrichimica Acta       Date:  2016       Impact factor: 3.667

7.  A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts.

Authors:  Linlin Qin; Bao Hu; Kiel D Neumann; Ethan J Linstad; Katelyenn McCauley; Jordan Veness; Jayson J Kempinger; Stephen G DiMagno
Journal:  European J Org Chem       Date:  2015-08-14

8.  Prediction of 19F NMR Chemical Shifts for Fluorinated Aromatic Compounds.

Authors:  Carla Saunders; Mohammad B Khaled; Jimmie D Weaver; Dean J Tantillo
Journal:  J Org Chem       Date:  2018-02-26       Impact factor: 4.354

9.  Photocatalytic C-F alkylation; facile access to multifluorinated arenes.

Authors:  A Singh; J J Kubik; J D Weaver
Journal:  Chem Sci       Date:  2015-09-29       Impact factor: 9.825

10.  Organophotoredox Hydrodefluorination of Trifluoromethylarenes with Translational Applicability to Drug Discovery.

Authors:  Jeroen B I Sap; Natan J W Straathof; Thomas Knauber; Claudio F Meyer; Maurice Médebielle; Laura Buglioni; Christophe Genicot; Andrés A Trabanco; Timothy Noël; Christopher W Am Ende; Véronique Gouverneur
Journal:  J Am Chem Soc       Date:  2020-05-11       Impact factor: 15.419

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