Reductive Umpolung of Carbonyl Derivatives with Visible-Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α-Amino Radicals and Ketyl Radicals

Eleonora Fava, Anthony Millet, Masaki Nakajima, Sebastian Loescher, Magnus Rueping

Research output: Contribution to journalArticlepeer-review

128 Scopus citations

Abstract

Visible-light-mediated photoredox-catalyzed aldimine-aniline and aldehyde-aniline couplings have been realized. The reductive single electron transfer (SET) umpolung of various carbonyl derivatives enabled the generation of intermediary ketyl and α-amino radical anions, which were utilized for the synthesis of unsymmetrically substituted 1,2-diamines and amino alcohols. Anilines can be coupled with aldimines or aldehydes in a visible-light-mediated photoredox-catalyzed process. Reductive single electron transfer (SET) umpolung of the carbonyl derivatives leads to the generation of intermediary ketyl and α-amino radical anions, which were used for the synthesis of unsymmetrically substituted 1,2-diamines and amino alcohols.
Original languageEnglish (US)
Pages (from-to)6776-6779
Number of pages4
JournalAngewandte Chemie International Edition
Volume55
Issue number23
DOIs
StatePublished - May 2 2016

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