Bromo- or Methoxy-Group-Promoted Umpolung Electron Transfer Enabled, Visible-Light-Mediated Synthesis of 2‑Substituted Indole-3-glyoxylates

A visible-light-mediated radical tandem cyclization of ortho-isocyano-α-bromo cinnamates to 2-substituted indole-3-glyoxylates is achieved by formation of both C–C/C–S and C–O bonds. The reaction proceeds through a hitherto unprecedented bromine- or methoxy-group-promoted umpolung back electron tran...

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Bibliographic Details
Published in:Organic letters 2018-11, Vol.20 (22), p.6984-6989
Main Authors: Vidyasagar, Adiyala, Shi, Jinwei, Kreitmeier, Peter, Reiser, Oliver
Format: Article
Language:English
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Summary:A visible-light-mediated radical tandem cyclization of ortho-isocyano-α-bromo cinnamates to 2-substituted indole-3-glyoxylates is achieved by formation of both C–C/C–S and C–O bonds. The reaction proceeds through a hitherto unprecedented bromine- or methoxy-group-promoted umpolung back electron transfer from an α-carbonyl radical to the photocatalyst. This method allows preparation of diverse 2-arylated or 2-thioarylated indole-3-glyoxylates. The glyoxylate group installed in the products can be utilized for several biologically relevant manipulations.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02725