Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 45, Pages 12064-12068Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201406450
Keywords
energy transfer; organocatalysis; photochemistry; radicals; synthetic methods
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Funding
- Institute of Chemical Research of Catalonia (ICIQ) Foundation
- European Research Council (ERC) under the European Community's Seventh Framework Program (FP7 2007-2013)/ERC [278541]
- Alma Mater Studiorum-Universita di Bologna (Italy)
- ICREA Funding Source: Custom
- European Research Council (ERC) [278541] Funding Source: European Research Council (ERC)
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We have found that an organic molecule as simple as p-anisaldehyde efficiently catalyzes the intermolecular atom-transfer radical addition (ATRA) of a variety of haloalkanes onto olefins, one of the fundamental carbon-carbon bond-forming transformations in organic chemistry. The reaction requires exceptionally mild reaction conditions to proceed, as it occurs at ambient temperature and under illumination by a readily available fluorescent light bulb. Initial investigations support a mechanism whereby the aldehydic catalyst photo-chemically generates the reactive radical species by sensitization of the organic halides by an energy-transfer pathway.
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