Literature DB >> 11667045

Nickel-Catalyzed Direct Electrochemical Cross-Coupling between Aryl Halides and Activated Alkyl Halides.

Muriel Durandetti1, Jean-Yves Nédélec, Jacques Périchon.   

Abstract

The electrochemical reduction of a mixture of aryl halides and activated alkyl halides in DMF in the presence of catalytic amount of NiBr(2)bipy leads to cross-coupling products in good to high yields. The method applies to the synthesis of alpha-aryl ketones, alpha-aryl esters, and allylated compounds from readily available organic halides. Optimization of the process has been obtained by slowly adding the most reactive organic halide (usually the activated alkyl halide) during the electrolysis which is best conducted at 70 degrees C when aryl bromides are involved.

Entities:  

Year:  1996        PMID: 11667045     DOI: 10.1021/jo9518314

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  22 in total

1.  Metallaphotoredox-Catalyzed Cross-Electrophile Csp3-Csp3 Coupling of Aliphatic Bromides.

Authors:  Russell T Smith; Xiaheng Zhang; Juan A Rincón; Javier Agejas; Carlos Mateos; Mario Barberis; Susana García-Cerrada; Oscar de Frutos; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2018-12-10       Impact factor: 15.419

2.  Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis.

Authors:  Travis J DeLano; Sarah E Reisman
Journal:  ACS Catal       Date:  2019-07-25       Impact factor: 13.084

3.  Nickel-catalyzed reductive conjugate addition to enones via allylnickel intermediates.

Authors:  Ruja Shrestha; Stephanie C M Dorn; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2013-01-08       Impact factor: 15.419

4.  Mechanism and selectivity in nickel-catalyzed cross-electrophile coupling of aryl halides with alkyl halides.

Authors:  Soumik Biswas; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2013-10-21       Impact factor: 15.419

5.  Generation of organolithium compounds bearing super silyl ester and their application to Matteson rearrangement.

Authors:  Susumu Oda; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-21       Impact factor: 15.336

6.  Monovalent Nickel-Mediated Radical Formation: A Concerted Halogen-Atom Dissociation Pathway Determined by Electroanalytical Studies.

Authors:  Qiao Lin; Yue Fu; Peng Liu; Tianning Diao
Journal:  J Am Chem Soc       Date:  2021-08-25       Impact factor: 15.419

7.  Selective cross-coupling of organic halides with allylic acetates.

Authors:  Lukiana L Anka-Lufford; Michael R Prinsell; Daniel J Weix
Journal:  J Org Chem       Date:  2012-11-06       Impact factor: 4.354

8.  Palladium-catalyzed α-arylation of zinc enolates of esters: reaction conditions and substrate scope.

Authors:  Takuo Hama; Shaozhong Ge; John F Hartwig
Journal:  J Org Chem       Date:  2013-08-21       Impact factor: 4.354

9.  Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Chlorides with Primary Alkyl Chlorides.

Authors:  Seoyoung Kim; Matthew J Goldfogel; Michael M Gilbert; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2020-05-21       Impact factor: 15.419

10.  Discovery of N-(3-fluoro-4-methylsulfonamidomethylphenyl)urea as a potent TRPV1 antagonistic template.

Authors:  Jihyae Ann; Wei Sun; Xing Zhou; Aeran Jung; Jisoo Baek; Sunho Lee; Changhoon Kim; Suyoung Yoon; Sunhye Hong; Sun Choi; Noe A Turcios; Brienna K A Herold; Timothy E Esch; Nancy E Lewin; Adelle Abramovitz; Larry V Pearce; Peter M Blumberg; Jeewoo Lee
Journal:  Bioorg Med Chem Lett       Date:  2016-06-07       Impact factor: 2.823

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