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Title

Deacylative alkylation vs. photoredox catalysis in the synthesis of 3,3'‐bioxindoles

AuthorsMoreno‐Cabrerizo, Cristina; Ortega‐Martínez, Aitor; Esteruelas, Miguel A. CSIC ORCID; López, Ana M. CSIC ORCID; Nájera, Carmen; Sansano, José M.
KeywordsPhotoredox catalysis
Bioxindoles
Iridium
Dacylative bromination
Deacylative alkylation
Issue Date29-May-2020
PublisherJohn Wiley & Sons
CitationEuropean Journal of Organic Chemistry 2020(20): 3101-3109 (2020)
AbstractThe synthesis of 3,3'‐bioxindoles employing deacylative alkylations (DaA) in one‐pot process, where the 3‐bromooxindoles are generated in situ, is described. Good yields and moderate diastereoselections are obtained. By the modification of this procedure the synthesis of pure 3‐bromooxindoles through a deacylative bromination (DaB) is achieved. These bromides are efficiently employed in a photoredox dimerization process to get the desired 3,3'‐bioxindoles in good yields and low diastereoselections. In this single‐electron‐transfer (SET) mechanism the presence of a high quantum‐yield iridium(III) complex ensures high conversions in short reaction times.
Publisher version (URL)https://doi.org/10.1002/ejoc.202000375
URIhttp://hdl.handle.net/10261/212312
DOI10.1002/ejoc.202000375
ISSN1434-193X
E-ISSN1099-0690
Appears in Collections:(ISQCH) Artículos

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