Issue 24, 2022

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

Abstract

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
22 sep. 2022
Accepted
19 okt. 2022
First published
20 okt. 2022

Org. Chem. Front., 2022,9, 6780-6785

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

J. Ni, M. Lanzi and A. W. Kleij, Org. Chem. Front., 2022, 9, 6780 DOI: 10.1039/D2QO01511K

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