Synthesis of sulfur heterocycles via domino metal-mediated reactions

GRAPHICAL ABSTRACT

ABSTRACT

Two methodologies to access S-heterocycles and mixed N,S-heterocycles via metal-mediated domino reactions are described. One involves a cyclocarbopalladation/cross-coupling domino process and leads to benzene-fused five- or six-membered sulfur heterocycles with a stereo defined tetrasubstituted exocyclic double bond. The other consists in a three-component domino reaction between 2-aminophenyl disulfide, copper cyanide, and an electrophile to access N-substituted 2-amino benzothiazoles. Preliminary results in the use of the second method to access N-substituted 2-imino benzothiazoles are also reported.

KEYWORDS:

• Sulfur heterocycles
• domino reactions
• palladium catalysis
• copper-mediated reaction
• sulfides
• thiocyanates

Acknowledgment

We thank Dr. Lydia Karmazin (analytical department of the University of Strasbourg) for X-ray analyses.

Funding

This project was supported by the University of Strasbourg (IDEX grant for T.C.) and the Centre National de la Recherche Scientifique (CNRS).