Title : Decatungstate catalyzed photochemical synthesis of 2-fluorosulfonyl derivatives
Abstract:
Sulfonyl fluorides exhibit remarkable stability and reactivity, rendering them suitable for various chemical environments, including physiological conditions. This unique property stems from the strong sulfur-fluorine bond, which has garnered significant attention in organic synthesis, drug discovery, and materials science. Ethene sulfonyl fluoride (ESF) is a pivotal compound in organic synthesis, boasting reactivity as a Michael acceptor and a candidate for sulfur(VI) fluoride exchange (SuFEx) click chemistry. However, the limited availability of nucleophiles restricts the potential of sulfonylation products. To address this limitation, we explored the use of tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer catalyst in C-H functionalization reactions, aiming to access a broader range of nucleophilic moieties for ESF functionalization. Notably, this approach yielded novel 2-fluorosulfonylethyl derivatives in moderate to good isolated yields. Furthermore, the methodology introduced a novel one-pot two-step synthesis of β-functionalized ketones and sulfonyl fluorides, which were subsequently employed in sulfur(VI) fluoride exchange (SuFEx) click chemistry. This enabled the synthesis of diverse derivatives, including sultones, sulfonamides, sulfonates, and sulphonyl azides.
