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. 2021 Jan 22;11(8):4593-4597.
doi: 10.1039/d1ra00063b. eCollection 2021 Jan 21.

Transition-metal-free decarboxylative thiolation of stable aliphatic carboxylates

Wei-Long Xing  1 , De-Guang Liu  1 , Ming-Chen Fu  1
Affiliations

Transition-metal-free decarboxylative thiolation of stable aliphatic carboxylates

Wei-Long Xing et al. RSC Adv. .

Abstract

A transition-metal-free decarboxylative thiolation protocol is reported in which primary, secondary, tertiary (hetero)aryl acetates and α-CN substituted acetates undergo the decarboxylative thiolation smoothly, to deliver a variety of functionalized aryl alkyl sulfides in moderate to excellent yields. Aryl diselenides are also amenable substrates for construction of C-Se bonds under the simple and mild reaction conditions. Moreover, the protocol is successfully applied to the late-stage modification of pharmaceutical carboxylates with satisfactory chemoselectivity and functional-group compatibility.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Thioether-containing pharmaceutical agents.
Scheme 1
Scheme 1. The initially hypothesized mechanism and the focus of this work.
Fig. 2
Fig. 2. The Gibbs free energies of the feasible mechanism.
See this image and copyright information in PMC

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