Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2021 Oct 18;60(43):23128-23133.
doi: 10.1002/anie.202108752. Epub 2021 Sep 16.

Ball-Milling-Enabled Reactivity of Manganese Metal*

William I Nicholson  1 , Joseph L Howard  1 , Giuseppina Magri  1 , Alex C Seastram  1 , Adam Khan  1 , Robert R A Bolt  2 , Louis C Morrill  1 , Emma Richards  1 , Duncan L Browne  2
Affiliations

Ball-Milling-Enabled Reactivity of Manganese Metal*

William I Nicholson et al. Angew Chem Int Ed Engl. .

Abstract

Efforts to generate organomanganese reagents under ball-milling conditions have led to the serendipitous discovery that manganese metal can mediate the reductive dimerization of arylidene malonates. The newly uncovered process has been optimized and its mechanism explored using CV measurements, radical trapping experiments, EPR spectroscopy, and solution control reactions. This unique reactivity can also be translated to solution whereupon pre-milling of the manganese is required.

Keywords: ball milling; electron paramagnetic spectroscopy; manganese; organometallics; reductive coupling.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Examples of using mechanochemistry to alter reactivity by different methods.
Scheme 2
Scheme 2
Substrate scope of the manganese mediated reductive dimerization of arylidene malonates by ball‐milling.
Scheme 3
Scheme 3
Mechanistic investigation of the manganese mediated reductive dimerization of arylidene malonates by ball‐milling.
Scheme 4
Scheme 4
Control experiments of solution versus milling for manganese activation.
See this image and copyright information in PMC

References

    1. None
    1. Williams M. T. J., Morrill L. C., Browne D. L., ACS Sustainable Chem. Eng. 2020, 8, 17876–17881; - PMC - PubMed
    1. Nicholson W. I., Seastram A. C., Iqbal S. A., Reed-Berendt B. G., Morrill L. C., Browne D. L., ChemSusChem 2020, 13, 131–135; - PMC - PubMed
    1. Rodríguez B., Bruckmann A., Bolm C., Chem. Eur. J. 2007, 13, 4710–4722; - PubMed
    1. Mack J., Shumba M., Green Chem. 2007, 9, 328–330;

Publication types

LinkOut - more resources