Literature DB >> 29460380

Iron-Catalyzed Cross-Couplings in the Synthesis of Pharmaceuticals: In Pursuit of Sustainability.

Aleksandra Piontek1, Elwira Bisz1, Michal Szostak1,2.   

Abstract

The scarcity of precious metals has led to the development of sustainable strategies for metal-catalyzed cross-coupling reactions. The establishment of new catalytic methods using iron is attractive owing to the low cost, abundance, ready availability, and very low toxicity of iron. In the last few years, sustainable methods for iron-catalyzed cross-couplings have entered the critical area of pharmaceutical research. Most notably, iron is one of the very few metals that have been successfully field-tested as highly effective base-metal catalysts in practical, kilogram-scale industrial cross-couplings. In this Minireview, we critically discuss the strategic benefits of using iron catalysts as green and sustainable alternatives to precious metals in cross-coupling applications for the synthesis of pharmaceuticals. The Minireview provides an essential introduction to the fundamental aspects of practical iron catalysis, highlights areas for improvement, and identifies new fields to be explored.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Grignard reagents; base-metal catalysis; cross-coupling; iron catalysis; sustainability

Mesh:

Substances:

Year:  2018        PMID: 29460380     DOI: 10.1002/anie.201800364

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


  23 in total

1.  Enabling Two-Electron Pathways with Iron and Cobalt: From Ligand Design to Catalytic Applications.

Authors:  Rebeca Arevalo; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2019-05-28       Impact factor: 15.419

2.  Direct Observation of Transmetalation from a Neutral Boronate Ester to a Pyridine(diimine) Iron Alkoxide.

Authors:  Paul O Peterson; Stephan M Rummelt; Bradley M Wile; S Chantal E Stieber; Hongyu Zhong; Paul J Chirik
Journal:  Organometallics       Date:  2019-12-23       Impact factor: 3.876

3.  The Effect of β-Hydrogen Atoms on Iron Speciation in Cross-Couplings with Simple Iron Salts and Alkyl Grignard Reagents.

Authors:  Jeffrey D Sears; Salvador B Muñoz; Stephanie L Daifuku; Ari A Shaps; Stephanie H Carpenter; William W Brennessel; Michael L Neidig
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-29       Impact factor: 15.336

4.  N-Heterocyclic Carbene Complexes of Nickel(II) from Caffeine and Theophylline: Sustainable Alternative to Imidazol-2-ylidenes.

Authors:  Jin Zhang; Mahbubur Rahman; Qun Zhao; Jessica Feliciano; Elwira Bisz; Błażej Dziuk; Roger Lalancette; Roman Szostak; Michal Szostak
Journal:  Organometallics       Date:  2022-04-05       Impact factor: 3.837

Review 5.  N-Heterocyclic Carbene Complexes in C-H Activation Reactions.

Authors:  Qun Zhao; Guangrong Meng; Steven P Nolan; Michal Szostak
Journal:  Chem Rev       Date:  2020-01-22       Impact factor: 60.622

6.  Oxidative Addition of Aryl and Alkyl Halides to a Reduced Iron Pincer Complex.

Authors:  Stephan M Rummelt; Paul O Peterson; Hongyu Zhong; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2021-04-08       Impact factor: 15.419

7.  Fe-catalyzed three-component dicarbofunctionalization of unactivated alkenes with alkyl halides and Grignard reagents.

Authors:  Lei Liu; Wes Lee; Cassandra R Youshaw; Mingbin Yuan; Michael B Geherty; Peter Y Zavalij; Osvaldo Gutierrez
Journal:  Chem Sci       Date:  2020-07-24       Impact factor: 9.825

8.  Organozinc pivalates for cobalt-catalyzed difluoroalkylarylation of alkenes.

Authors:  Xinyi Cheng; Xingchen Liu; Shengchun Wang; Ying Hu; Binjing Hu; Aiwen Lei; Jie Li
Journal:  Nat Commun       Date:  2021-07-16       Impact factor: 14.919

9.  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

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

Authors:  Peter G N Neate; Bufan Zhang; Jessica Conforti; William W Brennessel; Michael L Neidig
Journal:  Org Lett       Date:  2021-07-26       Impact factor: 6.072

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