Aminomethylations of electron-deficient compounds—bringing iron photoredox catalysis into play

Ilic, Aleksandra; Strücker, Benjamin R.; Johnson, Catherine E.; Hainz, Simon; Lomoth, Reiner; Wärnmark, Kenneth

doi:10.1039/d4sc02612h

Chem. Sci.

2024

DOI: 10.1039/d4sc02612h

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Aminomethylations of electron-deficient compounds—bringing iron photoredox catalysis into play

Aleksandra Ilic,

Benjamin R. Strücker,

Catherine E. Johnson

et al.

Abstract: Electron transfer to the 2LMCT state of a photoactive complex based on Earth-abundant iron has been used to drive photocatalytic aminomethylation reactions by generation of α-aminoalkyl radicals and the underlying mechanism has been investigated.

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Luminescent Fe(III) Complex Sensitizes Aerobic Photon Upconversion and Initiates Photocatalytic Radical Polymerization

Jin,

Xu,

Yan

et al. 2024

J. Am. Chem. Soc.

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Light energy conversion often relies on photosensitizers with long-lived excited states, which are mostly made of precious metals such as ruthenium or iridium. Photoactive complexes based on highly abundant iron seem attractive for sustainable energy conversion, but this remains very challenging due to the short excited state lifetimes of the current iron complexes. This study shows that a luminescent Fe(III) complex sensitizes triplet−triplet annihilation upconversion with anthracene derivatives via underexplored doublet-triplet energy transfer, which is assisted by preassociation between the photosensitizer and the annihilator. In the presence of an organic mediator, the green-toblue upconversion efficiency Φ UC with 9,10-diphenylanthracene (DPA) as the annihilator achieves a 6-fold enhancement to ∼0.2% in aerated solution at room temperature. The singlet excited state of DPA, accessed via photon upconversion in the Fe(III)/DPA pair, allows efficient photoredox catalytic radical polymerization of acrylate monomers in a spatially controlled manner, whereas this process is kinetically hindered with the prompt DPA. Our study provides a new strategy of using low-cost iron and low-energy visible light for efficient polymer synthesis, which is a significant step for both fundamental research and future applications.

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Luminescent Fe(III) Complex Sensitizes Aerobic Photon Upconversion and Initiates Photocatalytic Radical Polymerization

Jin,

Xu,

Yan

et al. 2024

J. Am. Chem. Soc.

View full text Add to dashboard Cite

show abstract

Visible light-induced cascade annulation of sulfoxonium ylides with azides for the synthesis of 2-trifluoromethyl indoles

Cui,

Chen,

Zhang

et al. 2025

Chem. Commun.

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Aminomethylations of electron-deficient compounds—bringing iron photoredox catalysis into play

Abstract: Electron transfer to the 2LMCT state of a photoactive complex based on Earth-abundant iron has been used to drive photocatalytic aminomethylation reactions by generation of α-aminoalkyl radicals and the underlying mechanism has been investigated.

Cited by 2 publications

References 78 publications

Luminescent Fe(III) Complex Sensitizes Aerobic Photon Upconversion and Initiates Photocatalytic Radical Polymerization

Luminescent Fe(III) Complex Sensitizes Aerobic Photon Upconversion and Initiates Photocatalytic Radical Polymerization

Visible light-induced cascade annulation of sulfoxonium ylides with azides for the synthesis of 2-trifluoromethyl indoles

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