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TMEDA in iron‐catalyzed hydromagnesiation : formation of iron(II)‐alkyl species for controlled reduction to alkene‐stabilized iron(0)
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Neate, Peter G. N., Greenhalgh, Mark D., Brennessel, William, Thomas, Stephen M. and Neidig, Michael (2020) TMEDA in iron‐catalyzed hydromagnesiation : formation of iron(II)‐alkyl species for controlled reduction to alkene‐stabilized iron(0). Angewandte Chemie International Edition . doi:10.1002/anie.202006639 ISSN 1433-7851.
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WRAP-TMEDA-iron‐catalyzed-hydromagnesiation-formation-iron(II)‐alkyl-species-controlled-reduction-alkene‐stabilized-iron(0)-Greenhalgh-2020.pdf - Accepted Version - Requires a PDF viewer. Download (1987Kb) | Preview |
Official URL: http://dx.doi.org/10.1002/anie.202006639
Abstract
N,N,N’,N’‐Tetramethylethylenediamine (TMEDA) has been one of the most prevalent and successful additives used in iron‐catalysis, finding application in reactions as diverse as cross‐coupling, C‐H activation and borylation. However, the role that TMEDA plays in these reactions remains largely undefined. Herein, studying the iron‐catalyzed hydromagnesiation of styrene derivatives using TMEDA has provided molecular‐level insight into the role of TMEDA in achieving effective catalysis. Key is the initial formation of TMEDA‐iron(II) alkyl species which undergo a controlled reduction to selectively form catalytically active styrene‐stabilized iron(0)‐alkyl complexes. While TMEDA is not bound to the catalytically active species, these active iron(0) complexes cannot be accessed in the absence of TMEDA. This mode of action, allowing for controlled reduction and access to iron(0) species, represents a new paradigm for the role of this important reaction additive in iron catalysis.
Item Type: | Journal Article | |||||||||
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Subjects: | Q Science > QD Chemistry | |||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | |||||||||
Library of Congress Subject Headings (LCSH): | Iron catalysts, Iron, Catalysis, Organometallic chemistry, Chemical engineering, Alkaloids | |||||||||
Journal or Publication Title: | Angewandte Chemie International Edition | |||||||||
Publisher: | Wiley - V C H Verlag GmbH & Co. KGaA | |||||||||
ISSN: | 1433-7851 | |||||||||
Official Date: | 15 June 2020 | |||||||||
Dates: |
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DOI: | 10.1002/anie.202006639 | |||||||||
Status: | Peer Reviewed | |||||||||
Publication Status: | Published | |||||||||
Reuse Statement (publisher, data, author rights): | This is the peer reviewed version of the following article: Neate, P..G.N., Greenhalgh, M., Brennessel, W., Thomas, S..P. and Neidig, M. (2020), TMEDA in Iron‐Catalyzed Hydromagnesiation: Formation of Iron(II)‐Alkyl Species for Controlled Reduction to Alkene‐Stabilized Iron(0). Angew. Chem. Int. Ed. doi:10.1002/anie.202006639, which has been published in final form at https://doi.org/10.1002/anie.202006639. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. | |||||||||
Access rights to Published version: | Restricted or Subscription Access | |||||||||
Date of first compliant deposit: | 23 June 2020 | |||||||||
Date of first compliant Open Access: | 15 June 2021 | |||||||||
RIOXX Funder/Project Grant: |
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