Literature DB >> 25588092

Atom-economical transformation of diaryliodonium salts: tandem C-H and N-H arylation of indoles.

Sachin G Modha1, Michael F Greaney.   

Abstract

Arylation using diaryliodonium salts generates one equivalent of an iodoarene as a side-product, a significant waste of atom economy. Here, we show that diaryliodoniums can undergo Cu-catalyzed tandem C-H/N-H arylation, producing novel indoles that incorporate both aryl groups from the reagent.

Entities:  

Year:  2015        PMID: 25588092     DOI: 10.1021/ja5124754

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  17 in total

1.  Transition-Metal-Free C3 Arylation of Indoles with Aryl Halides.

Authors:  Ji Chen; Jimmy Wu
Journal:  Angew Chem Int Ed Engl       Date:  2017-03-03       Impact factor: 15.336

2.  Stereoselective Direct N-Trifluoropropenylation of Heterocycles with a Hypervalent Iodonium Reagent.

Authors:  János T Csenki; Ádám Mészáros; Zsombor Gonda; Zoltán Novák
Journal:  Chemistry       Date:  2021-10-06       Impact factor: 5.020

3.  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

4.  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

5.  Mild and selective base-free C-H arylation of heteroarenes: experiment and computation.

Authors:  Hannes P L Gemoets; Indrek Kalvet; Alexander V Nyuchev; Nico Erdmann; Volker Hessel; Franziska Schoenebeck; Timothy Noël
Journal:  Chem Sci       Date:  2016-09-05       Impact factor: 9.825

6.  Palladium-catalyzed direct β-arylation of ketones with diaryliodonium salts: a stoichiometric heavy metal-free and user-friendly approach.

Authors:  Zhongxing Huang; Quynh P Sam; Guangbin Dong
Journal:  Chem Sci       Date:  2015-06-17       Impact factor: 9.825

7.  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

8.  Combining Sanford Arylations on Benzodiazepines with the Nuisance Effect.

Authors:  Raysa Khan; Sarote Boonseng; Paul D Kemmitt; Robert Felix; Simon J Coles; Graham J Tizzard; Gareth Williams; Olivia Simmonds; Jessica-Lily Harvey; John Atack; Hazel Cox; John Spencer
Journal:  Adv Synth Catal       Date:  2017-08-02       Impact factor: 5.837

Review 9.  Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis.

Authors:  Gwendal Grelier; Benjamin Darses; Philippe Dauban
Journal:  Beilstein J Org Chem       Date:  2018-06-21       Impact factor: 2.883

10.  Cu-catalyzed N-3-Arylation of Hydantoins Using Diaryliodonium Salts.

Authors:  Linn Neerbye Berntsen; Ainara Nova; David S Wragg; Alexander H Sandtorv
Journal:  Org Lett       Date:  2020-03-23       Impact factor: 6.005

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