Literature DB >> 28634609

SNAr catalysis enhanced by an aromatic donor-acceptor interaction; facile access to chlorinated polyfluoroarenes.

Sameera Senaweera1, Jimmie D Weaver.   

Abstract

Selective catalytic SNAr reaction of polyfluoroaryl C-F bonds with chloride is shown. Stoichiometric TMSCl makes the reaction exergonic and allows catalysis, which involves ground state elevation of chloride, aromatic donor-acceptor interactions, and stabilization of the Meisenheimer complex. Traditional cross-coupling of the products is now possible and demonstrates the utility.

Entities:  

Year:  2017        PMID： 28634609      PMCID： PMC5549941          DOI： 10.1039/c7cc03996d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  10 in total

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2.  The Principle of Microscopic Reversibility.

Authors:  R C Tolman
Journal:  Proc Natl Acad Sci U S A       Date:  1925-07       Impact factor: 11.205

3.  C-F bond activation in organic synthesis.

Authors:  Hideki Amii; Kenji Uneyama
Journal:  Chem Rev       Date:  2009-05       Impact factor: 60.622

4.  Catalytic SNAr reaction of non-activated fluoroarenes with amines via Ru eta6-arene complexes.

Authors:  Maiko Otsuka; Kohei Endo; Takanori Shibata
Journal:  Chem Commun (Camb)       Date:  2009-11-26       Impact factor: 6.222

5.  Computational and Experimental Studies of Regioselective SNAr Halide Exchange (Halex) Reactions of Pentachloropyridine.

Authors:  Robert D J Froese; Gregory T Whiteker; Thomas H Peterson; Daniel J Arriola; James M Renga; Justin W Shearer
Journal:  J Org Chem       Date:  2016-11-02       Impact factor: 4.354

6.  Accelerated arene ligand exchange in the (Arene)Cr(CO)2L series.

Authors:  M F Semmelhack; Anatoly Chlenov; Douglas M Ho
Journal:  J Am Chem Soc       Date:  2005-06-01       Impact factor: 15.419

7.  Exploring and exploiting polar-π interactions with fluorinated aromatic amino acids.

Authors:  Christopher J Pace; Jianmin Gao
Journal:  Acc Chem Res       Date:  2012-10-24       Impact factor: 22.384

8.  π-π interaction assisted hydrodefluorination of perfluoroarenes by gold hydride: a case of synergistic effect on C-F bond activation.

Authors:  Hongbin Lv; Jin-Hui Zhan; Yuan-Bo Cai; Yi Yu; Bingwu Wang; Jun-Long Zhang
Journal:  J Am Chem Soc       Date:  2012-09-25       Impact factor: 15.419

9.  Anhydrous Tetramethylammonium Fluoride for Room-Temperature S(N)Ar Fluorination.

Authors:  Sydonie D Schimler; Sarah J Ryan; Douglas C Bland; John E Anderson; Melanie S Sanford
Journal:  J Org Chem       Date:  2015-12-09       Impact factor: 4.354

10.  Catalytic SNAr of unactivated aryl chlorides.

Authors:  James W Walton; Jonathan M J Williams
Journal:  Chem Commun (Camb)       Date:  2015-02-18       Impact factor: 6.222
  10 in total
  3 in total

1.  Controlled chemoselective defluorination and non-defluorination for [5 + 1] aromatic annulation via Meisenheimer-type nitrogen anion and radical intermediates.

Authors:  Jinlong Qian; Jinlong Zhang; Huameng Yang; Lei Kang; Gaoxi Jiang
Journal:  Chem Sci       Date:  2019-08-07       Impact factor: 9.825

2.  NHC-BIAN-Cu(I)-Catalyzed Friedländer-Type Annulation of 2-Amino-3-(per)fluoroacetylpyridines with Alkynes on Water.

Authors:  Magdalena Dolna; Michał Nowacki; Oksana Danylyuk; Artur Brotons-Rufes; Albert Poater; Michał Michalak
Journal:  J Org Chem       Date:  2022-04-08       Impact factor: 4.198

3.  Theoretical Prediction and Explanation of Reaction Site Selectivity in the Addition of a Phenoxy Group to Perfluoropyrimidine, Perfluoropyridazine, and Perfluoropyrazine.

Authors:  Timothy J Fuhrer; Matthew Houck; Rachel M Chapman; Scott T Iacono
Journal:  Molecules       Date:  2021-12-16       Impact factor: 4.411
  3 in total

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