Iron(0)-Mediated Stereoselective (3+2)-Cycloaddition of Thiochalcones via a Diradical Intermediate

Buday P, Seeber P, Zens C, Abul-Futouh H, Goerls H, Gräfe S, Matczak P, Kupfer S, Weigand W, Mloston G (2020)

Publication Type: Journal article

Publication year: 2020

Journal

Chemistry - A European Journal Wiley

Book Volume: 26

Pages Range: 11412-11416

Journal Issue: 50

DOI: 10.1002/chem.202001412

Abstract

Reactions of α,β-unsaturated aromatic thioketones 1 (thiochalcones) with Fe3(CO)12 leading to η⁴-1-thia-1,3-diene iron tricarbonyl complexes 2, [FeFe] hydrogenase mimics 3, and the thiopyrane adduct 4 are described. Obtained products have been characterized by X-ray crystallography and by computational methods. Completely regio- and diastereoselective formation of the five-membered ring system in products 3, containing four stereogenic centers, can be explained by an unprecedented, stepwise (3+2)-cycloaddition of two thiochalcone molecules mediated by Fe3(CO)12. Quantum chemical calculations aimed at elucidation of the reaction mechanism, suggest that the formal (3+2)-cycloaddition proceeds via sequential intramolecular radical transfer events upon homolytic cleavage of one carbon-sulfur bond leading to a diradical intermediate.

Involved external institutions

Friedrich-Schiller-Universität Jena

Germany (DE) Al-Zaytoonah University of Jordan (ZUJ) / جامعة الزيتونة الأردنية

Jordan (JO) University of Lodz / Uniwersytet Łódzki

Poland (PL)

How to cite

APA:

Buday, P., Seeber, P., Zens, C., Abul-Futouh, H., Goerls, H., Gräfe, S.,... Mloston, G. (2020). Iron(0)-Mediated Stereoselective (3+2)-Cycloaddition of Thiochalcones via a Diradical Intermediate. Chemistry - A European Journal, 26(50), 11412-11416. https://doi.org/10.1002/chem.202001412

MLA:

Buday, Philipp, et al. "Iron(0)-Mediated Stereoselective (3+2)-Cycloaddition of Thiochalcones via a Diradical Intermediate." Chemistry - A European Journal 26.50 (2020): 11412-11416.

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