NDLI: Synthetic Applications of Photoinduced Electron Transfer Decarboxylation Reactions

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Synthetic Applications of Photoinduced Electron Transfer Decarboxylation Reactions

Content Provider	Semantic Scholar
Author	Griesbeck, Axel G. Kramer, Wolfgang Oelgemoeller, Michael
Copyright Year	1999
Abstract	Photoinduced electron transfer (PET) decarboxylation of alkyl carboxylates in water leads to primary, secondary or tertiary carbon radicals which undergo C-C coupling reactions either in an intraor intermolecular fashion. Intramolecular coupling gives rise to heterocyclic ring systems (lactams, lactones, cyclopeptides, cyclic ethers, crown ethers) with ring sizes from 5 to 28 and a broad variety of functionalities. Intermolecular coupling gives Grignardtype adducts (but with different chemoand regioselectivities as for carbanion reactions). Yields of these reactions are mostly high, dilution conditions are not necessary, quantum yields are in the range of 0.5-0.6, and chemoas well as regioselectivities are excellent. The electron-accepting chromophores which have been investigated are the imides of phthalic, maleic, quinolinic and trimellitic acid. Selectivity can be further controlled by two simple tricks: Only triplet excited acceptors are active in these electron-transfer reactions, thus sensitization excludes other (homolytic) pathways; Donor groups (SR, NR 2, aryl, OR, C=C) other than the carboxylate can be activated by lowering the pH (and thus protonating the COO-donor). In intramolecular reactions, substrate concentration up to 0.1 M were applied successfully and the reactions were completed in 1012 h for multigram conversions.
Starting Page	1169
Ending Page	1178
Page Count	10
File Format	PDF HTM / HTML
DOI	10.1002/chin.199939256
Volume Number	30
Alternate Webpage(s)	https://www.thieme-connect.com/products/ejournals/pdf/10.1055/s-1999-3159.pdf
Alternate Webpage(s)	https://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-1999-3159.pdf
Alternate Webpage(s)	https://doi.org/10.1002/chin.199939256
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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