| Title: |
Aminomethylations of electron-deficient compounds : bringing iron photoredox catalysis into play |
| Authors: |
Ilic, Aleksandra; Strücker, Benjamin R.; Johnson, Catherine E.; Hainz, Simon; Lomoth, Reiner; Wärnmark, Kenneth |
| Publisher Information: |
Uppsala universitet, Fysikalisk kemi; Lund Univ, Ctr Anal & Synth CAS, Dept Chem, SE-22100 Lund, Sweden. |
| Publication Year: |
2024 |
| Collection: |
Uppsala University: Publications (DiVA) |
| Subject Terms: |
Organic Chemistry; Organisk kemi; Atom and Molecular Physics and Optics; Atom- och molekylfysik och optik |
| Description: |
The α-functionalisation of N-containing compounds is an area of broad interest in synthetic chemistry due to their presence in biologically active substances among others. Visible light-induced generation of nucleophilic α-aminoalkyl radicals as reactive intermediates that can be trapped by electron-deficient alkenes presents an attractive and mild approach to achieve said functionalisation. In this work, [Fe(III)(phtmeimb)2]PF6 (phtmeimb = phenyl(tris(3-methylimidazol-2-ylidene))borate), an N-heterocyclic carbene (NHC) complex based on Earth-abundant iron, was used as photoredox catalyst to efficiently drive the formation of α-aminoalkyl radicals from a range of different α-trimethylsilylamines and their subsequent addition to a number of electron-deficient alkenes under green light irradiation. Mechanistic investigations elucidated the different reaction steps of the complete photocatalytic cycle. In terms of yields and substrate scope, we show that [Fe(III)(phtmeimb)2]PF6 can compete with noble metal photoredox catalysts, for instance outcompeting archetypal [Ru(bpy)3]Cl2 under comparable reaction conditions, illustrating that iron photocatalysts can efficiently facilitate photoredox reactions of synthetic value. |
| Document Type: |
article in journal/newspaper |
| File Description: |
application/pdf |
| Language: |
English |
| Relation: |
Chemical Science, 2041-6520, 2024, 15:30, s. 12077-12085; PMID 39092117; ISI:001261895400001 |
| DOI: |
10.1039/d4sc02612h |
| Availability: |
http://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-540961; https://doi.org/10.1039/d4sc02612h |
| Rights: |
info:eu-repo/semantics/openAccess |
| Accession Number: |
edsbas.CB3FF06F |
| Database: |
BASE |