Literature DB >> 21319835

Room temperature, metal-free synthesis of diaryl ethers with use of diaryliodonium salts.

Nazli Jalalian1, Eloisa E Ishikawa, Luiz F Silva, Berit Olofsson.   

Abstract

A fast, high-yielding synthesis of diaryl ethers with use of mild and metal-free conditions has been developed. The scope includes bulky ortho-substituted diaryl ethers, which are difficult to obtain by metal-catalyzed protocols. Halo-substituents, racemization-prone amino acid derivatives, and heteroaromatics are also tolerated. The methodology is expected to be of high utility in the synthesis of complex molecules and in the pharmaceutical industry.

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Year:  2011        PMID: 21319835     DOI: 10.1021/ol200265t

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


  15 in total

1.  Synthesis of Functionalized Dihydrobenzofurans by Direct Aryl C-O Bond Formation under Mild Conditions.

Authors:  Joseph Alvarado; Jeremy Fournier; Armen Zakarian
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-18       Impact factor: 15.336

2.  Metal-free arylation of ethyl acetoacetate with hypervalent diaryliodonium salts: an immediate access to diverse 3-aryl-4(1H)-quinolones.

Authors:  Andrii Monastyrskyi; Niranjan K Namelikonda; Roman Manetsch
Journal:  J Org Chem       Date:  2015-02-24       Impact factor: 4.354

3.  Selective Targeting of Heme Protein in Cytochrome P450 and Nitric Oxide Synthase by Diphenyleneiodonium.

Authors:  John T Szilagyi; Vladimir Mishin; Diane E Heck; Yi-Hua Jan; Lauren M Aleksunes; Jason R Richardson; Ned D Heindel; Debra L Laskin; Jeffrey D Laskin
Journal:  Toxicol Sci       Date:  2016-02-14       Impact factor: 4.849

4.  Mechanistic Investigations of Cu-Catalyzed Fluorination of Diaryliodonium Salts: Elaborating the CuI/CuIII Manifold in Copper Catalysis.

Authors:  Naoko Ichiishi; Allan J Canty; Brian F Yates; Melanie S Sanford
Journal:  Organometallics       Date:  2014-09-22       Impact factor: 3.876

5.  Flow Synthesis of Diaryliodonium Triflates.

Authors:  Gabriele Laudadio; Hannes P L Gemoets; Volker Hessel; Timothy Noël
Journal:  J Org Chem       Date:  2017-07-20       Impact factor: 4.354

6.  Iodine(III) Reagents in Radical Chemistry.

Authors:  Xi Wang; Armido Studer
Journal:  Acc Chem Res       Date:  2017-06-21       Impact factor: 22.384

7.  Arylation with unsymmetrical diaryliodonium salts: a chemoselectivity study.

Authors:  Joel Malmgren; Stefano Santoro; Nazli Jalalian; Fahmi Himo; Berit Olofsson
Journal:  Chemistry       Date:  2013-06-20       Impact factor: 5.236

8.  Room temperature, metal-free arylation of aliphatic alcohols.

Authors:  Raju Ghosh; Erik Lindstedt; Nazli Jalalian; Berit Olofsson
Journal:  ChemistryOpen       Date:  2014-04-11       Impact factor: 2.911

9.  A counteranion triggered arylation strategy using diaryliodonium fluorides.

Authors:  L Chan; A McNally; Q Y Toh; A Mendoza; M J Gaunt
Journal:  Chem Sci       Date:  2014-11-12       Impact factor: 9.825

10.  Metal-free formal synthesis of phenoxazine.

Authors:  Gabriella Kervefors; Antonia Becker; Chandan Dey; Berit Olofsson
Journal:  Beilstein J Org Chem       Date:  2018-06-20       Impact factor: 2.883

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