Mechanistic study of styrene aziridination by iron(IV) nitrides

Crandell, Douglas W.; Muñoz, Salvador B.; Smith, Jeremy M.; Baik, Mu-Hyun

doi:10.1039/c8sc03677b

Title: Mechanistic study of styrene aziridination by iron(IV) nitrides

Journal Article · 10 September 2018 · Chemical Science

DOI: https://doi.org/10.1039/c8sc03677b · OSTI ID:1471749

Crandell, Douglas W. ^[1]; Muñoz, Salvador B. ^[2];

^[2];

^[3]

Indiana Univ., Bloomington, IN (United States); Saint Louis Univ., St. Louis, MO (United States)
Indiana Univ., Bloomington, IN (United States)
Institute for Basic Science (IBS), Daejeon (Korea, Republic of); Korea Advanced Inst. Science and Technology (KAIST), Daejeon (Korea, Republic of)

A combined experimental and computational investigation was undertaken to investigate the mechanism of aziridination of styrene by the tris(carbene)borate iron(IV) nitride complex, PhB(^tBuIm)₃FeN. While mechanistic investigations suggest that aziridination occurs via a reversible, stepwise pathway, it was not possible to confirm the mechanism using only experimental techniques. Density functional theory calculations support a stepwise radical addition mechanism, but suggest that a low-lying triplet (S = 1) state provides the lowest energy path for C–N bond formation (24.6 kcal mol^-1) and not the singlet ground (S = 0) state. A second spin flip may take place in order to facilitate ring closure and the formation of the quintet (S = 2) aziridino product. A Hammett analysis shows that electron-withdrawing groups increase the rate of reaction σ_p (ρ = 1.2 ± 0.2). This finding is supported by the computational results, which show that the rate-determining step drops from 24.6 kcal mol^-1 to 18.3 kcal mol^-1 when (p-NO₂C₆H₄)CHCH₂ is used and slightly increases to 25.5 kcal mol^-1 using (p-NMe₂C₆H₄)CHCH₂ as the substrate.

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Research Organization:: New Mexico State Univ., Las Cruces, NM (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); Institute for Basic Science in Korea

Grant/Contract Number:: FG02-08ER15996; IBS-R10-D1

OSTI ID:: 1471749

Alternate ID(s):: OSTI ID: 1609964

Journal Information:: Chemical Science, Vol. 9, Issue 45; ISSN 2041-6520

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 14 works

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Rationalization of the Barrier Height for p -Z-styrene Epoxidation by Iron(IV)-Oxo Porphyrin Cation Radicals with Variable Axial Ligands Kumar, Devesh; Latifi, Reza; Kumar, Suresh Inorganic Chemistry, Vol. 52, Issue 14 https://doi.org/10.1021/ic4005104	journal	July 2013
Mechanism of the Iron-Mediated Alkene Aziridination Reaction: Experimental and Computational Investigations Klotz, Katie L.; Slominski, Luke M.; Riemer, Miranda E. Inorganic Chemistry, Vol. 48, Issue 3 https://doi.org/10.1021/ic8020244	journal	February 2009
[4 + 1] Cycloadditions of Cyclohexadienes with Osmium Nitrides Maestri, Aaron G.; Cherry, Kevin S.; Toboni, Joseph J. Journal of the American Chemical Society, Vol. 123, Issue 30 https://doi.org/10.1021/ja016111v	journal	August 2001
New Class of Nucleophiles for Palladium-Catalyzed Asymmetric Allylic Alkylation. Total Synthesis of Agelastatin A Trost, Barry M.; Dong, Guangbin Journal of the American Chemical Society, Vol. 128, Issue 18 https://doi.org/10.1021/ja061105q	journal	May 2006
Synthesis of Aziridines from Alkenes and Aryl Azides with a Reusable Macrocyclic Tetracarbene Iron Catalyst Cramer, S. Alan; Jenkins, David M. Journal of the American Chemical Society, Vol. 133, Issue 48 https://doi.org/10.1021/ja2090965	journal	December 2011
What Factors Influence the Rate Constant of Substrate Epoxidation by Compound I of Cytochrome P450 and Analogous Iron(IV)-Oxo Oxidants? Kumar, Devesh; Karamzadeh, Baharan; Sastry, G. Narahari Journal of the American Chemical Society, Vol. 132, Issue 22 https://doi.org/10.1021/ja9106176	journal	June 2010
Four-Electron Oxidation of Phenols to p -Benzoquinone Imines by a (Salen)ruthenium(VI) Nitrido Complex Xie, Jianhui; Man, Wai-Lun; Wong, Chun-Yuen Journal of the American Chemical Society, Vol. 138, Issue 18 https://doi.org/10.1021/jacs.6b02923	journal	April 2016
An Iron(II) Ylide Complex as a Masked Open-Shell Iron Alkylidene Species in Its Alkylidene-Transfer Reactions with Alkenes Liu, Jian; Hu, Lianrui; Wang, Lei Journal of the American Chemical Society, Vol. 139, Issue 10 https://doi.org/10.1021/jacs.7b00484	journal	March 2017
Mechanism of Chemical and Electrochemical N ₂ Splitting by a Rhenium Pincer Complex Lindley, Brian M.; van Alten, Richt S.; Finger, Markus Journal of the American Chemical Society, Vol. 140, Issue 25 https://doi.org/10.1021/jacs.8b03755	journal	May 2018
NR Transfer Reactivity of Azo-Compound I of P450. How Does the Nitrogen Substituent Tune the Reactivity of the Species toward CH and CC Activation? Moreau, Yohann; Chen, Hui; Derat, Etienne The Journal of Physical Chemistry B, Vol. 111, Issue 34 https://doi.org/10.1021/jp0743065	journal	August 2007
Mononuclear iron complexes relevant to nonheme iron oxygenases. Synthesis, characterizations and reactivity of Fe-Oxo and Fe-Peroxo intermediates Thibon, Aurore; Bartoli, Jean-François; Bourcier, Sophie Dalton Transactions, Issue 43 https://doi.org/10.1039/b913470k	journal	January 2009
A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu Grimme, Stefan; Antony, Jens; Ehrlich, Stephan The Journal of Chemical Physics, Vol. 132, Issue 15 https://doi.org/10.1063/1.3382344	journal	April 2010
An FeIVO complex of a tetradentate tripodal nonheme ligand Lim, M. H.; Rohde, J. -U.; Stubna, A. Proceedings of the National Academy of Sciences, Vol. 100, Issue 7 https://doi.org/10.1073/pnas.0636830100	journal	March 2003

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Fe‐Based Complexes as Styrene Aziridination Catalysts: Ligand Substitution Tunes Catalyst Activity Coin, Guillaume; Patra, Ranjan; Clémancey, Martin ChemCatChem, Vol. 11, Issue 21 https://doi.org/10.1002/cctc.201901211	journal	March 2019

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