CAS 1186018-19-8, Cat. No EN300-46591695
Reagent for photochemical amination of thioethers and sulfoxides
Tces3 (shortly for trichloroethoxysulfonyl azide) is a reagent for amination in the photochemical (UVA) continuous flow process of thioethers and sulfoxides[1], [2]. Sulfilimines and sulfoximines are highly valuable building blocks due to their importance in biologically active agents and this reagent offers a simple solution with high yields. The reaction proceeds at room temperature with a residence time below 2 hours using UVA light[1], [2]. A chiral reagent is also compatible with these reaction conditions to produce easily separable diastereomeric sulfilimines. The Tces protecting group could be easily cleaved from sulfoximine using zinc in acetic acid to afford free sulfoximine[1].
Synonyms: 2,2,2-Trichloroethoxysulfonyl azide
Selected publication
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Iron-Catalyzed Amination of Sulfides and Sulfoxides with Azides in Photochemical Continuous Flow Synthesis.
Lebel H.; Piras H.; Borduy M. ACS Catal 2016, 6 (2), 1109–1112. DOI: 10.1021/acscatal.5b02495
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2,2,2-Trichloroethoxysulfonyl Azide.
Lebel H. Encyclopedia of Reagents for Organic Synthesis 2017, 1–2. DOI: 10.1002/047084289X.rn02034