2-Methyltetrahydrofuran: A Green Solvent for Iron-Catalyzed Cross-Coupling Reactions

ChemSusChem
Elwira Bisz, Michal Szostak

Abstract

Iron-catalyzed cross-coupling reactions allow sustainable formation of C-C bonds using cost-effective, earth-abundant base-metal catalysis for complex syntheses of pharmaceuticals, natural products, and fine chemicals. The major challenge to maintain full sustainability of the process is the identification of green and renewable solvents that can be harnessed to replace the conventional solvents for this highly attractive reaction. Herein, iron-catalyzed cross-coupling of aryl chlorides and tosylates with challenging organometallic reagents possessing β-hydrogens is found to proceed in good to excellent yields with the green, sustainable, and eco-friendly 2-methyltetrahydrofuran (2-MeTHF) as solvent. The reaction operates with excellent functional group tolerance under very mild conditions. Furthermore, large-scale cross-coupling, cross-coupling of heteroaromatic substrates, and cross-coupling of challenging aryl tosylates and carbamates mediated by Fe-N-heterocyclic carbene catalytic systems in eco-friendly 2-MeTHF were also carried out. The developed method was applied to the key cross-coupling in the synthesis of a fibrinolysis inhibitor, further highlighting the potential of 2-MeTHF as a general solvent for sustainable iron...Continue Reading

References

Nov 15, 2002·Journal of the American Chemical Society·Alois FürstnerHelga Krause
Jan 28, 2003·Angewandte Chemie·Alois Fürstner, Andreas Leitner
Nov 13, 2003·Angewandte Chemie·Alois FürstnerJon T Jensen
May 22, 2004·The Journal of Organic Chemistry·Günter SeidelAlois Fürstner
Dec 16, 2004·Chemical Communications : Chem Comm·Robin B BedfordMichael Hird
Apr 22, 2005·Angewandte Chemie·Alois Fürstner, Laurent Turet
Aug 16, 2005·Chemical Communications : Chem Comm·Robin B BedfordMichael Hird
May 1, 2007·Angewandte Chemie·Gérard CahiezAlban Moyeux
Jul 28, 2007·Angewandte Chemie·Amandine GuérinotJanine Cossy
Jul 31, 2007·Journal of the American Chemical Society·Takuji Hatakeyama, Masaharu Nakamura
Jul 1, 2008·Accounts of Chemical Research·Benjamin D Sherry, Alois Fürstner
Sep 5, 2008·Proceedings of the National Academy of Sciences of the United States of America·Chao-Jun Li, Barry M Trost
Dec 11, 2008·Angewandte Chemie·Waldemar Maximilian CzaplikAxel Jacobi von Wangelin
Mar 20, 2009·Journal of the American Chemical Society·Yang-Hui ZhangJin-Quan Yu
May 9, 2009·ChemSusChem·Waldemar Maximilian CzaplikAxel Jacobi von Wangelin
Sep 30, 2009·Organic Letters·Thomas M GøgsigTroels Skrydstrup
Dec 22, 2009·Chemical Society Reviews·Paul Anastas, Nicolas Eghbali
Feb 13, 2010·Chemical Reviews·Gérard Cahiez, Alban Moyeux
Dec 8, 2010·Chemical Reviews·Brad M RosenVirgil Percec
Feb 22, 2011·Nature Materials·Eiichi Nakamura, Kentaro Sato
Mar 25, 2011·Current Medicinal Chemistry·V R Solomon, H Lee
Oct 29, 2011·Chemical Society Reviews·Roger A Sheldon
Jan 4, 2012·Angewandte Chemie·Samet Gülak, Axel Jacobi von Wangelin
Jul 5, 2012·Organic Letters·Amanda L SilbersteinNeil K Garg
Aug 1, 2012·ACS Chemical Biology·Perry A Frey, George H Reed
Apr 17, 2013·Journal of Medicinal Chemistry·Marian C BryanHelen F Sneddon
Sep 18, 2014·Organic Letters·Toolika Agrawal, Silas P Cook
Mar 10, 2015·Chemical Reviews·Ingmar Bauer, Hans-Joachim Knölker
Apr 29, 2015·Accounts of Chemical Research·Robin B Bedford
May 9, 2015·Journal of the American Chemical Society·Masayoshi JinMasaharu Nakamura
Jun 30, 2015·Chemical Reviews·Angeles FarránRobert J Linhardt
Jul 18, 2015·Angewandte Chemie·Dominik GärtnerAxel Jacobi von Wangelin
Sep 24, 2015·Natural Product Reports·Julien Legros, Bruno Figadère
Jan 6, 2016·Proceedings. Mathematical, Physical, and Engineering Sciences·Tom Welton
Aug 18, 2016·Angewandte Chemie·Ksenia S Egorova, Valentine P Ananikov
Apr 6, 2017·Chemical Reviews·Rui ShangEiichi Nakamura
Aug 26, 2017·ChemSusChem·Elwira Bisz, Michal Szostak

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Citations

Feb 21, 2018·Angewandte Chemie·Aleksandra PiontekMichal Szostak
Nov 7, 2018·Acta Crystallographica. Section C, Structural Chemistry·Aleksandra PiontekMichal Szostak
Jan 16, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Elwira Bisz, Michal Szostak
Mar 23, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Joana F CamposSabine Berteina-Raboin

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