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Deacylative Alkylation vs. Photoredox Catalysis in the Synthesis of 3,3'‐Bioxindoles
Author(s) -
MorenoCabrerizo Cristina,
OrtegaMartínez Aitor,
Esteruelas Miguel A.,
López Ana M.,
Nájera Carmen,
Sansano José M.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000375
Subject(s) - chemistry , alkylation , photoredox catalysis , yield (engineering) , halogenation , iridium , combinatorial chemistry , catalysis , quantum yield , electron transfer , photocatalysis , photochemistry , organic chemistry , materials science , physics , quantum mechanics , metallurgy , fluorescence
The 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.