Synthesis of 2-Cyanobenzothiazoles via Pd-Catalyzed/Cu-Assisted C-H Functionalization/Intramolecular C-S Bond Formation from N-Arylcyanothioformamides |
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Authors: | Nathan Broudic Alexandra Pacheco-Benichou Corinne Fruit Thierry Besson |
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Affiliation: | Univ Rouen Normandie, INSA Rouen, CNRS, COBRA UMR 6014, 76000 Rouen, France |
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Abstract: | We report herein on a catalytic system involving palladium and copper to achieve the cyclization of N-arylcyanothioformamides and the synthesis of 2-cyanobenzothiazoles. The C-H functionalization/intramolecular C-S bond formation reaction was achieved in the presence of air, using 2.0 equiv of an inorganic additive (KI). In many cases, the reaction led to a sole product regioselectively obtained in good yields, allowing the synthesis of a wide range of substituted 2-cyanobenzothiazole derivatives, providing valuable building blocks for the design of more complex heterocyclic or molecular labeling systems. |
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Keywords: | N-arylcyanothioformamides 4 5-dichloro-1 2 3-dithiazolium chloride N-arylimino-1 2 3-dithiazoles 2-cyanobenzothiazoles C-S bond formation |
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