Literature DB >> 23244161

Iron-catalyzed cross-coupling reactions of alkyl Grignards with aryl sulfamates and tosylates.

Toolika Agrawal1, Silas P Cook.   

Abstract

The iron-catalyzed cross-coupling of aryl sulfamates and tosylates has been achieved with primary and secondary alkyl Grignards. This study of iron-catalyzed cross-coupling reactions also examines the isomerization and β-hydride elimination problems that are associated with the use of isopropyl nucleophiles. While a variety of iron sources were competent in the reaction, the use of FeF(3)•3H(2)O was critical to minimize nucleophile isomerization.

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Year:  2012        PMID: 23244161     DOI: 10.1021/ol303130j

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


  9 in total

1.  Intermediates and Reactivity in Iron-Catalyzed Cross-Couplings of Alkynyl Grignards with Alkyl Halides.

Authors:  Jared L Kneebone; William W Brennessel; Michael L Neidig
Journal:  J Am Chem Soc       Date:  2017-05-16       Impact factor: 15.419

2.  Combined Effects of Backbone and N-Substituents on Structure, Bonding, and Reactivity of Alkylated Iron(II)-NHCs.

Authors:  Salvador B Muñoz; Valerie E Fleischauer; William W Brennessel; Michael L Neidig
Journal:  Organometallics       Date:  2018-09-06       Impact factor: 3.876

3.  Synthesis of N-Substituted Sulfamate Esters from Sulfamic Acid Salts by Activation with Triphenylphosphine Ditriflate.

Authors:  J Miles Blackburn; Melanie A Short; Thomas Castanheiro; Suraj K Ayer; Tobias D Muellers; Jennifer L Roizen
Journal:  Org Lett       Date:  2017-11-03       Impact factor: 6.005

4.  Iron-catalyzed arylation of heterocycles via directed C-H bond activation.

Authors:  John J Sirois; Riley Davis; Brenton DeBoef
Journal:  Org Lett       Date:  2014-01-22       Impact factor: 6.005

5.  NHC and nucleophile chelation effects on reactive iron(ii) species in alkyl-alkyl cross-coupling.

Authors:  Valerie E Fleischauer; Salvador B Muñoz Iii; Peter G N Neate; William W Brennessel; Michael L Neidig
Journal:  Chem Sci       Date:  2018-01-08       Impact factor: 9.825

6.  Iron-catalysed allylation-hydrogenation sequences as masked alkyl-alkyl cross-couplings.

Authors:  Josef Bernauer; Guojiao Wu; Axel Jacobi von Wangelin
Journal:  RSC Adv       Date:  2019-10-02       Impact factor: 4.036

7.  NHC Effects on Reduction Dynamics in Iron-Catalyzed Organic Transformations*.

Authors:  Nikki J Wolford; Salvador B Muñoz; Peter G N Neate; William W Brennessel; Michael L Neidig
Journal:  Chemistry       Date:  2021-08-04       Impact factor: 5.020

8.  Iron(II) Active Species in Iron-Bisphosphine Catalyzed Kumada and Suzuki-Miyaura Cross-Couplings of Phenyl Nucleophiles and Secondary Alkyl Halides.

Authors:  Stephanie L Daifuku; Jared L Kneebone; Benjamin E R Snyder; Michael L Neidig
Journal:  J Am Chem Soc       Date:  2015-08-26       Impact factor: 15.419

9.  Phenol Derivatives as Coupling Partners with Alkylsilicates in Photoredox/Nickel Dual Catalysis.

Authors:  Niki R Patel; Gary A Molander
Journal:  J Org Chem       Date:  2016-06-03       Impact factor: 4.354

  9 in total

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