Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 5, Pages 1485-1489Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201409529
Keywords
alkylation; indoles; 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/ERC [278541]
- MINECO for support through the Severo Ochoa Excellence Accreditation [SEV-2013-0319]
- MECD [FPU13/02402]
- European Research Council (ERC) [278541] Funding Source: European Research Council (ERC)
- ICREA Funding Source: Custom
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A metal-free, photochemical strategy for the direct alkylation of indoles was developed. The reaction, which occurs at ambient temperature, is driven by the photochemical activity of electron donor-acceptor (EDA) complexes, generated upon association of substituted 1H-indoles with electron-accepting benzyl and phenacyl bromides. Significant mechanistic insights are provided by the X-ray single-crystal analysis of an EDA complex relevant to the photoalkylation and the determination of the quantum yield (Phi) of the process.
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