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Intranet

Unusual DBU-catalyzed decarboxylative formation of allylic thioethers from vinyl cyclic carbonates and thiols

An unanticipated exo-cyclic nucleophilic attack of thiol reagents on vinyl cyclic carbonates is described under DBU catalysis. The process allows the production of allylic thioethers under moderately mild conditions following a sequence of steps that involve a nucleophilic attack of the thiol on the C-terminus of the C[double bond, length as m-dash]C bond, carbonate ring-opening, and decarboxylation followed by final protonation. This unusual thiol-induced ring-opening complements the previously reported and more widely observed endo-cyclic nucleophilic attack on either the carbonate or methylene carbon centers, and therefore amplifies the reactivity modes that can be accessed with these heterocycles.

Ni, J.; Lanzi, M.; Kleij, A. W.

Org. Chem. Front. 2022, 9,
DOI: 10.1039/D2QO01511K

Associated ICIQ research group/s:

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