Literature DB >> 25966029

Metal-free N-arylation of secondary amides at room temperature.

Fredrik Tinnis1, Elin Stridfeldt1, Helena Lundberg1, Hans Adolfsson1, Berit Olofsson1,2.   

Abstract

The arylation of secondary acyclic amides has been achieved with diaryliodonium salts under mild and metal-free conditions. The methodology has a wide scope, allows synthesis of tertiary amides with highly congested aryl moieties, and avoids the regioselectivity problems observed in reactions with (diacetoxyiodo)benzene.

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Year:  2015        PMID： 25966029     DOI： 10.1021/acs.orglett.5b01079

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


  12 in total

1.  O-Cyclopropyl hydroxylamines: gram-scale synthesis and utility as precursors for N-heterocycles.

Authors:  Kaitlyn Lovato; Urmibhusan Bhakta; Yi Pin Ng; László Kürti
Journal:  Org Biomol Chem       Date:  2020-05-06       Impact factor: 3.876

2.  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

3.  Iodine(III) Reagents in Radical Chemistry.

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

Review 4.  Synthesis of spirocyclic scaffolds using hypervalent iodine reagents.

Authors:  Fateh V Singh; Priyanka B Kole; Saeesh R Mangaonkar; Samata E Shetgaonkar
Journal:  Beilstein J Org Chem       Date:  2018-07-17       Impact factor: 2.883

5.  The Synthesis of 2-Aminobenzoxazoles Using Reusable Ionic Liquid as a Green Catalyst under Mild Conditions.

Authors:  Ya Zhou; Zhiqing Liu; Tingting Yuan; Jianbin Huang; Chenjiang Liu
Journal:  Molecules       Date:  2017-04-02       Impact factor: 4.411

6.  Regiospecific N-Arylation of Aliphatic Amines under Mild and Metal-Free Reaction Conditions.

Authors:  Nibadita Purkait; Gabriella Kervefors; Erika Linde; Berit Olofsson
Journal:  Angew Chem Int Ed Engl       Date:  2018-07-26       Impact factor: 15.336

7.  Sterically Congested 2,6-Disubstituted Anilines from Direct C-N Bond Formation at an Iodine(III) Center.

Authors:  Nicola Lucchetti; Michelangelo Scalone; Serena Fantasia; Kilian Muñiz
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

8.  Base-catalyzed synthesis of aryl amides from aryl azides and aldehydes.

Authors:  Sheng Xie; Yang Zhang; Olof Ramström; Mingdi Yan
Journal:  Chem Sci       Date:  2015-10-22       Impact factor: 9.825

9.  One-pot synthesis of diaryliodonium salts from arenes and aryl iodides with Oxone-sulfuric acid.

Authors:  Natalia Soldatova; Pavel Postnikov; Olga Kukurina; Viktor V Zhdankin; Akira Yoshimura; Thomas Wirth; Mekhman S Yusubov
Journal:  Beilstein J Org Chem       Date:  2018-04-12       Impact factor: 2.883

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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