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Repairing the thiol-ene coupling reaction.
Journal article

Repairing the thiol-ene coupling reaction.

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  • 2014-03-12
Published in:
  • Angewandte Chemie (International ed. in English). - 2014
allylic compounds
boranes
glycosides
radical reactions
synthetic methods
Allyl Compounds
Boranes
Combinatorial Chemistry Techniques
Glycosides
Molecular Structure
Stereoisomerism
Thioglucosides
English Thiol-ene coupling (TEC) reactions emerged as one of the most useful processes for coupling different molecular units under reaction mild conditions. However, TEC reactions involving weak CH bonds (allylic and benzylic fragments) are difficult to run and often low yielding. Mechanistic studies demonstrate that hydrogen-atom transfer processes at allylic and benzylic positions are responsible for the lack of efficiency of the radical-chain process. These competing reactions cannot be prevented, but reported herein is a method to repair the chain process by running the reaction in the presence of triethylborane and catechol. Under these reaction conditions, a unique repair mechanism leads to an efficient chain reaction, which is demonstrated with a broad range of anomeric O-allyl sugar derivatives including mono-, di-, and tetrasaccharides bearing various functionalities and protecting groups.
Language
  • English
Open access status
closed
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Persistent URL
https://sonar.ch/global/documents/79885
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