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Photoredox catalysi...
Photoredox catalysis via consecutive 2LMCT- and 3MLCT-excitation of an Fe(iii/ii)–N-heterocyclic carbene complex
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- Ilic, Aleksandra (author)
- Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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- Schwarz, Jesper (author)
- Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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- Johnson, Catherine (author)
- Uppsala University,Uppsala universitet,Fysikalisk kemi
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- de Groot, Lisa H.M. (author)
- Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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- Kaufhold, Simon (author)
- Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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- Lomoth, Reiner (author)
- Uppsala University,Uppsala universitet,Fysikalisk kemi
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- Wärnmark, Kenneth (author)
- Lund University,Lunds universitet,NanoLund: Centre for Nanoscience,Annan verksamhet, LTH,Lunds Tekniska Högskola,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,LTH profilområde: Nanovetenskap och halvledarteknologi,LTH profilområden,Other operations, LTH,Faculty of Engineering, LTH,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH,LTH Profile Area: Nanoscience and Semiconductor Technology,LTH Profile areas,Faculty of Engineering, LTH
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(creator_code:org_t)
- 2022
- 2022
- English.
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In: Chemical Science. - : Royal Society of Chemistry. - 2041-6520 .- 2041-6539. ; 13:32, s. 9165-9175
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Abstract
Subject headings
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- Fe-N-heterocyclic carbene (NHC) complexes attract increasing attention as photosensitisers and photoredox catalysts. Such applications generally rely on sufficiently long excited state lifetimes and efficient bimolecular quenching, which leads to there being few examples of successful usage of Fe-NHC complexes to date. Here, we have employed [Fe(iii)(btz)(3)](3+) (btz = (3,3 '-dimethyl-1,1 '-bis(p-tolyl)-4,4 '-bis(1,2,3-triazol-5-ylidene))) in the addition of alkyl halides to alkenes and alkynes via visible light-mediated atom transfer radical addition (ATRA). Unlike other Fe-NHC complexes, [Fe(iii/ii)(btz)(3)](3+/2+) benefits from sizable charge transfer excited state lifetimes >= 0.1 ns in both oxidation states, and the Fe(iii) (LMCT)-L-2 and Fe(ii) (MLCT)-M-3 states are strong oxidants and reductants, respectively. The combined reactivity of both excited states enables efficient one-electron reduction of the alkyl halide substrate under green light irradiation. The two-photon mechanism proceeds via reductive quenching of the Fe(iii) (LMCT)-L-2 state by a sacrificial electron donor and subsequent excitation of the Fe(ii) product to its highly reducing (MLCT)-M-3 state. This route is shown to be more efficient than the alternative, where oxidative quenching of the less reducing Fe(iii) (LMCT)-L-2 state by the alkyl halide drives the reaction, in the absence of a sacrificial electron donor.
Subject headings
- NATURVETENSKAP -- Kemi -- Teoretisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Theoretical Chemistry (hsv//eng)
- NATURVETENSKAP -- Kemi -- Fysikalisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Physical Chemistry (hsv//eng)
- NATURVETENSKAP -- Fysik -- Atom- och molekylfysik och optik (hsv//swe)
- NATURAL SCIENCES -- Physical Sciences -- Atom and Molecular Physics and Optics (hsv//eng)
Publication and Content Type
- ref (subject category)
- art (subject category)
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