2,2,2-Trichloroethyl N-tosyloxycarbamate

CAS 931109-52-3, Cat. No EN300-21834963
Reagent for amination and aziridination

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2,2,2-Trichloroethyl N-tosyloxycarbamate (Troc-NH-O-Ts) is a bench-stable N-sulfonyloxycarbamate reagent used as a metal–nitrene precursor for C–H amination and aziridination reactions¹. Under basic conditions in the presence of dirhodium catalysts, it generates reactive metal–nitrene species that enable direct C(sp³)–H amidation via insertion, forming Troc-protected amines with moderate to good yields and broad functional-group tolerance^2,3. The reagent is specifically designed to suppress intramolecular side reactions (no δ-C–H bonds), enabling efficient intermolecular C–H functionalization of benzylic, aliphatic, and heteroatom-adjacent positions. It is also effective in aziridination of alkenes and related nitrene-transfer processes, typically under mild conditions (base, metal catalyst), providing protected nitrogen-containing products⁴. Additionally, N-(tosyloxy)carbamates can serve as preformed nitrogen sources in oxyamination of alkenes, affording vicinal amino alcohol derivatives with good regioselectivity⁵. Ir-catalyzed amidation of silyl ketene acetals by the reagent proceeds to the formation of α-amido esters⁶. α-Amidation applies to both α-aryl and α-alkyl esters. A key advantage is the Troc protecting group, which can be readily removed under mild reductive conditions to give free amines, making the reagent highly practical for synthesis and late-stage functionalization.

Synonyms: [(2,2,2-trichloroethoxy)carbonyl]azanyl 4-methylbenzenesulfonate; 2,2,2-trichloroethyl (tosyloxy)carbamate; 2,2,2-trichloroethyl N-tosyloxycarbamate; Troc-NH-O-Ts; 2,2,2-trichloroethyl N-[(4-methylbenzenesulfonyl)oxy]carbamate; benzenesulfonic acid, 4-methyl-, [(2,2,2-trichloroethoxy)carbonyl]azanyl ester