Visible light photoredox organocatalysis: a fully transition metal-free direct asymmetric α-alkylation of aldehydes

Rose Bengal, a dye sensitizer, was found to be active as a visible light photoredox catalyst for the direct enantioselective alpha -alkylation of aldehydes in environmentally benign and simple conditions. Starting from a SOMO converse mechanism, the catalytic activity of the imidazolidinone organoca...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2012-01, Vol.14 (5), p.1293-1297
Main Authors: FIDALY, Kassim, CEBALLOS, Claire, FALGUIERES, Annie, SYLLA-IYARRETA VEITIA, Maité, GUY, Alain, FERROUD, Clotilde
Format: Article
Language:English
Subjects:
Catalysis
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Kinetics and mechanisms
Organic chemistry
Photochemistry
Physical chemistry of induced reactions (with radiations, particles and ultrasonics)
Preparations and properties
Reactivity and mechanisms
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:Rose Bengal, a dye sensitizer, was found to be active as a visible light photoredox catalyst for the direct enantioselective alpha -alkylation of aldehydes in environmentally benign and simple conditions. Starting from a SOMO converse mechanism, the catalytic activity of the imidazolidinone organocatalyst was improved using an electrophilic cocatalyst. The resulting methodology and optimal conditions led to efficient and transition-metal-free direct photoredox organocatalysis.
ISSN:1463-9262
1463-9270
DOI:10.1039/c2gc35118h