Application of Visible-to-UV Photon Upconversion to Photoredox Catalysis: The Activation of Aryl Bromides

Application of Visible-to-UV Photon Upconversion to Photoredox Catalysis: The Activation of Aryl Bromides

The activation of aryl–Br bonds was achieved by sequential combination of a triplet–triplet annihilation process of the organic dyes, butane‐2,3‐dione and 2,5‐diphenyloxazole, with a single‐electron‐transfer activation of aryl bromides. The photophysical and chemical steps were studied by time‐resol...

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Bibliographic Details
Published in:Chemistry : a European journal Vol. 21; no. 44; pp. 15496 - 15501
Main Authors: Majek, Michal, Faltermeier, Uwe, Dick, Bernhard, Pérez-Ruiz, Raúl, Jacobi von Wangelin, Axel
Format: Journal Article
Language:English
Published: Weinheim WILEY-VCH Verlag 26-10-2015
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
Subjects:
Activation
Aromatic compounds
aryl halides
Bromides
Chemistry
defunctionalization
Mathematical analysis
organocatalysis
photocatalysis
Photons
Pulsed lasers
Quenching
triplet states
two-photon process
Upconversion
organocatalysis
triplet states
two-photon process
aryl halides
photocatalysis
defunctionalization
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Summary:The activation of aryl–Br bonds was achieved by sequential combination of a triplet–triplet annihilation process of the organic dyes, butane‐2,3‐dione and 2,5‐diphenyloxazole, with a single‐electron‐transfer activation of aryl bromides. The photophysical and chemical steps were studied by time‐resolved transient fluorescence and absorption spectroscopy with a pulsed laser, quenching experiments, and DFT calculations. Two‐photon process: The combination of a visible‐to‐UV photon upconversion with a chemical electron‐transfer reaction mechanism has been applied to the reductive aryl–Br σ‐bond activation. Spectroscopic, preparative, and theoretical studies support the operation of a triplet–triplet annihilation process and sequential electron transfer and H‐atom‐transfer steps (see figure).
Bibliography:DFG Graduate School Photocatalysis
ArticleID:CHEM201502698
E.U. - No. PIEF-GA-2013-625064
ark:/67375/WNG-B2J9JHLT-X
Marie Curie program
istex:FAEE39712AA01CDDF73D52701C13B31BFE51683A
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201502698