Cover Image

Synthesis of Naphthylpyridines from Unsymmetrical Naphthylheptadiynes and the Configurational Stability of the Biaryl Axis

A series of different unsymmetrically substituted naphthyl-based diynes were synthesized. These substrates formed the foundation for the assembly of novel biaryls containing pyridine moieties with differently substituted five-membered rings in the backbone of the newly formed heterobiaryl system. Th...

Full description

Saved in:
Bibliographic Details
Main Authors: Fischer, Fabian (Author) , Siegle, Alexander Florian (Author) , Checinski, Marek (Author) , Fischer, Christine (Author) , Kral, Karolin (Author) , Thede, Richard (Author) , Trapp, Oliver (Author) , Hapke, Marko (Author)
Format: Article (Journal)
Language:English
Published: March 21, 2016
In: The journal of organic chemistry
Year: 2016, Volume: 81, Issue: 8, Pages: 3087-3102
ISSN:1520-6904
DOI:10.1021/acs.joc.5b02190
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.joc.5b02190
Get full text
Author Notes:Fabian Fischer, Alexander F. Siegle, Marek Checinski, Christine Fischer, Karolin Kral, Richard Thede, Oliver Trapp, Marko Hapke
Description
Summary:A series of different unsymmetrically substituted naphthyl-based diynes were synthesized. These substrates formed the foundation for the assembly of novel biaryls containing pyridine moieties with differently substituted five-membered rings in the backbone of the newly formed heterobiaryl system. The key step for their efficient construction was the photo- and cobalt-catalyzed [2 + 2 + 2] cycloaddition reaction between the corresponding naphthyldiyne and aceto- or benzonitrile. The heterobiaryl products have been isolated and investigated with respect to the configurational stability of their biaryl axis using dynamic chiral HPLC; subtle effects of the substitution pattern on the stability of the axis were observed. For several compounds the activation barriers (ΔG‡) of racemization were determined. Suitable substitution of the five-membered ring backbone exemplarily allowed the Co-catalyzed enantioselective cyclization to yield the enantiomerically enriched heterobiaryl.
Item Description:Gesehen am 19.05.2020
Physical Description:Online Resource
ISSN:1520-6904
DOI:10.1021/acs.joc.5b02190

Similar Items