Literature DB >> 25378244

Rapid and efficient copper-catalyzed Finkelstein reaction of (hetero)aromatics under continuous-flow conditions.

Mao Chen1, Saki Ichikawa, Stephen L Buchwald.   

Abstract

A general, rapid, and efficient method for the copper-catalyzed Finkelstein reaction of (hetero)aromatics has been developed using continuous flow to generate a variety of aryl iodides. The described method can tolerate a broad spectrum of functional groups, including N-H and O-H groups. Additionally, in lieu of isolation, the aryl iodide solutions were used in two distinct multistep continuous-flow processes (amidation and Mg-I exchange/nucleophilic addition) to demonstrate the flexibility of this method.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  copper; cross-coupling; flow chemistry; synthetic methods

Year:  2014        PMID: 25378244     DOI: 10.1002/anie.201409595

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  9 in total

1.  Photo-induced iodination of aryl halides under very mild conditions.

Authors:  Lu Li; Wenbo Liu; Xiaoyue Mu; Zetian Mi; Chao-Jun Li
Journal:  Nat Protoc       Date:  2016-09-15       Impact factor: 13.491

2.  Simple, Efficient and Controllable Synthesis of Iodo/Di-iodoarenes via Ipsoiododecarboxylation/Consecutive Iodination Strategy.

Authors:  Yun Yang; Lijuan Zhang; Guo-Jun Deng; Hang Gong
Journal:  Sci Rep       Date:  2017-01-16       Impact factor: 4.379

3.  Practical and economic lithiations of functionalized arenes and heteroarenes using Cy2NLi in the presence of Mg, Zn or La halides in a continuous flow.

Authors:  Matthias R Becker; Maximilian A Ganiek; Paul Knochel
Journal:  Chem Sci       Date:  2015-08-10       Impact factor: 9.825

4.  Transition-metal-free decarboxylative bromination of aromatic carboxylic acids.

Authors:  Jacob M Quibell; Gregory J P Perry; Diego M Cannas; Igor Larrosa
Journal:  Chem Sci       Date:  2018-03-26       Impact factor: 9.825

5.  Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings.

Authors:  Gregory J P Perry; Jacob M Quibell; Adyasha Panigrahi; Igor Larrosa
Journal:  J Am Chem Soc       Date:  2017-08-08       Impact factor: 15.419

6.  Continuous Flow Synthesis of High Valuable N-Heterocycles via Catalytic Conversion of Levulinic Acid.

Authors:  Daily Rodríguez-Padrón; Alain R Puente-Santiago; Alina M Balu; Mario J Muñoz-Batista; Rafael Luque
Journal:  Front Chem       Date:  2019-02-26       Impact factor: 5.221

7.  Catalyst shuttling enabled by a thermoresponsive polymeric ligand: facilitating efficient cross-couplings with continuously recyclable ppm levels of palladium.

Authors:  Erfei Wang; Mao Chen
Journal:  Chem Sci       Date:  2019-07-23       Impact factor: 9.825

8.  Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes.

Authors:  Stacey Webster; Kerry M O'Rourke; Conor Fletcher; Sally L Pimlott; Andrew Sutherland; Ai-Lan Lee
Journal:  Chemistry       Date:  2017-12-14       Impact factor: 5.236

Review 9.  Metal-Mediated Halogen Exchange in Aryl and Vinyl Halides: A Review.

Authors:  Gwilherm Evano; Antoine Nitelet; Pierre Thilmany; Damien F Dewez
Journal:  Front Chem       Date:  2018-04-26       Impact factor: 5.221

  9 in total

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