Literature DB >> 34310141

Dilithium Amides as a Modular Bis-Anionic Ligand Platform for Iron-Catalyzed Cross-Coupling.

Peter G N Neate1, Bufan Zhang1, Jessica Conforti1, William W Brennessel1, Michael L Neidig1.   

Abstract

Dilithium amides have been developed as a bespoke and general ligand for iron-catalyzed Kumada-Tamao-Corriu cross-coupling reactions, their design taking inspiration from previous mechanistic and structural studies. They allow for the cross-coupling of alkyl Grignard reagents with sp2-hybridized electrophiles as well as aryl Grignard reagents with sp3-hybridized electrophiles. This represents a rare example of a single iron-catalyzed system effective across diverse coupling reactions without significant modification of the catalytic protocol, as well as remaining operationally simple.

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Year:  2021        PMID: 34310141      PMCID: PMC8628259          DOI: 10.1021/acs.orglett.1c02053

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.072


  19 in total

1.  Gram-Scale, Cheap, and Eco-Friendly Iron-Catalyzed Cross-Coupling between Alkyl Grignard Reagents and Alkenyl or Aryl Halides.

Authors:  Gérard Cahiez; Guillaume Lefèvre; Alban Moyeux; Olivier Guerret; Eric Gayon; Loïc Guillonneau; Nicolas Lefèvre; Qinzhuo Gu; Edouard Zhou
Journal:  Org Lett       Date:  2019-04-09       Impact factor: 6.005

2.  The N-Methylpyrrolidone (NMP) Effect in Iron-Catalyzed Cross-Coupling with Simple Ferric Salts and MeMgBr.

Authors:  Salvador B Muñoz; Stephanie L Daifuku; Jeffrey D Sears; Tessa M Baker; Stephanie H Carpenter; William W Brennessel; Michael L Neidig
Journal:  Angew Chem Int Ed Engl       Date:  2018-05-08       Impact factor: 15.336

3.  Iron catalysis in organic synthesis.

Authors:  Ingmar Bauer; Hans-Joachim Knölker
Journal:  Chem Rev       Date:  2015-03-09       Impact factor: 60.622

4.  TMEDA in iron-catalyzed Kumada coupling: amine adduct versus homoleptic "ate" complex formation.

Authors:  Robin B Bedford; Peter B Brenner; Emma Carter; Paul M Cogswell; Mairi F Haddow; Jeremy N Harvey; Damien M Murphy; Joshua Nunn; Christopher H Woodall
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-21       Impact factor: 15.336

Review 5.  Iron-promoted C-C bond formation in the total synthesis of natural products and drugs.

Authors:  Julien Legros; Bruno Figadère
Journal:  Nat Prod Rep       Date:  2015-09-23       Impact factor: 13.423

6.  How low does iron go? Chasing the active species in fe-catalyzed cross-coupling reactions.

Authors:  Robin B Bedford
Journal:  Acc Chem Res       Date:  2015-04-28       Impact factor: 22.384

7.  A combined Mössbauer, magnetic circular dichroism, and density functional theory approach for iron cross-coupling catalysis: electronic structure, in situ formation, and reactivity of iron-mesityl-bisphosphines.

Authors:  Stephanie L Daifuku; Malik H Al-Afyouni; Benjamin E R Snyder; Jared L Kneebone; Michael L Neidig
Journal:  J Am Chem Soc       Date:  2014-06-11       Impact factor: 15.419

8.  Iron-catalyzed cross-coupling of primary and secondary alkyl halides with aryl grignard reagents.

Authors:  Masaharu Nakamura; Keiko Matsuo; Shingo Ito; Eiichi Nakamura
Journal:  J Am Chem Soc       Date:  2004-03-31       Impact factor: 15.419

9.  Intermediates and Mechanism in Iron-Catalyzed Cross-Coupling.

Authors:  Jeffrey D Sears; Peter G N Neate; Michael L Neidig
Journal:  J Am Chem Soc       Date:  2018-09-18       Impact factor: 15.419

10.  Multinuclear iron-phenyl species in reactions of simple iron salts with PhMgBr: identification of Fe4(μ-Ph)6(THF)4 as a key reactive species for cross-coupling catalysis.

Authors:  Stephanie H Carpenter; Tessa M Baker; Salvador B Muñoz; William W Brennessel; Michael L Neidig
Journal:  Chem Sci       Date:  2018-08-24       Impact factor: 9.825

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