The synthesis of functionalized azetidines from azetines is poorly explored. Here, we report the safe and sustainable continuous flow hydrogenation of 2-azetines using ethyl acetate and CPME as environmentally responsible solvents. The chemoselective saturation of the endocyclic double bond of 2-azetines bearing additional functional groups sensitive to hydrogenation has been additionally disclosed. Moreover, the protocol has been successfully combined with the continuous flow preparation of the substrates, accessing to a bio-relevant azetidine through a telescoped multistep approach.
A sustainable and chemoselective continuous flow hydrogenation of functionalized 2-azetines to azetidines / Graziano, Elena; Cannillo, Debora; Spennacchio, Mauro; Musci, Pantaleo; Pisano, Luisa; Andresini, Michael; Colella, Marco. - In: TETRAHEDRON GREEN CHEM. - ISSN 2773-2231. - 1:(2023), p. 100003. [10.1016/j.tgchem.2023.100003]
A sustainable and chemoselective continuous flow hydrogenation of functionalized 2-azetines to azetidines
Pisano, Luisa;
2023-01-01
Abstract
The synthesis of functionalized azetidines from azetines is poorly explored. Here, we report the safe and sustainable continuous flow hydrogenation of 2-azetines using ethyl acetate and CPME as environmentally responsible solvents. The chemoselective saturation of the endocyclic double bond of 2-azetines bearing additional functional groups sensitive to hydrogenation has been additionally disclosed. Moreover, the protocol has been successfully combined with the continuous flow preparation of the substrates, accessing to a bio-relevant azetidine through a telescoped multistep approach.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
