Palladium-Catalyzed C-H Bond Arylation and O-to N -Alkyl Migratory Rearrangement of 2-Alkoxythiazoles: One-Pot Access to 2-Alkoxy-5-arylthiazoles or 3-Alkyl-5-arylthiazol-2(3 H )-ones - UFR SPM Sciences et Propriétés de la Matière Accéder directement au contenu
Article Dans Une Revue Synthesis: Journal of Synthetic Organic Chemistry Année : 2022

Palladium-Catalyzed C-H Bond Arylation and O-to N -Alkyl Migratory Rearrangement of 2-Alkoxythiazoles: One-Pot Access to 2-Alkoxy-5-arylthiazoles or 3-Alkyl-5-arylthiazol-2(3 H )-ones

Résumé

Pd-catalyzed direct arylation of 2-alkylthiazoles is a well-known reaction affording the corresponding 2-alkyl-5-arylthiazoles in very high yields. Conversely, the reactivity of 2-alkoxythiazoles has not been described yet. Herein, we report conditions for the Pd-catalyzed regioselective C5-arylation of 2-alkoxythiazoles. Moreover, we also found reaction conditions leading to 3-alkyl-5-arylthiazol-2(3H)-ones via a one-pot direct arylation with an O- to N-alkyl migratory rearrangement. The judicious choice of reaction temperature and time allows control over the selectivity of the reaction. In general, at 100 °C, 2-alkoxy-5-arylthiazoles were the major products, whereas, at 120 °C with a longer reaction time, 3-alkyl-5-arylthiazol-2(3H)-ones were obtained with good selectivities. The arylation reaction is promoted by a ligand-free air-stable palladium catalyst and a simple and inexpensive base, without oxidant or further additives, and tolerates a variety of useful substituents on the aryl bromide and also heteroaryl bromides.
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Dates et versions

hal-03629842 , version 1 (27-09-2022)

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Hai-Yun Huang, Haoran Li, Marie Cordier, Henri Doucet. Palladium-Catalyzed C-H Bond Arylation and O-to N -Alkyl Migratory Rearrangement of 2-Alkoxythiazoles: One-Pot Access to 2-Alkoxy-5-arylthiazoles or 3-Alkyl-5-arylthiazol-2(3 H )-ones. Synthesis: Journal of Synthetic Organic Chemistry, 2022, 54 (8), pp.2037-2048. ⟨10.1055/s-0041-1737326⟩. ⟨hal-03629842⟩
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