4.7 Article

Synthesis of 2-aminothiazoles via rhodium-catalyzed carbenoid insertion/annulation of sulfoxonium ylides with thioureas

Journal

CHINESE CHEMICAL LETTERS
Volume 32, Issue 8, Pages 2555-2558

Publisher

ELSEVIER SCIENCE INC
DOI: 10.1016/j.cclet.2021.02.052

Keywords

2-Aminothiazoles; Carbene; Rhodium; Sulfoxonium ylides; Annulation

Funding

  1. National Natural Science Foundation of China [81373259, 81573286]
  2. Sichuan Science and Technology Program [2020YJ0221, 2018JY0537]

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This study demonstrates the efficient coupling of sulfoxonium ylides with thioureas under rhodium catalysis to produce 2-aminothiazoles with good functional group tolerance. This approach provides a convenient method for accessing a variety of 2-aminothiazole derivatives with high chemoselectivity.
Sulfoxonium ylides as carbene precursors couple smoothly with thioureas in the presence of 5 mol% of rhodium(II) acetate dimmer via carbenoid insertion to afford the corresponding 2-aminothiazoles with high chemoselectivity, providing a facile and efficient approach to access a variety of 2-aminothiazole derivatives with good functional groups tolerance. (c) 2021 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

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