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. 2025 Jul 11;90(27):9513-9518.
doi: 10.1021/acs.joc.5c00900. Epub 2025 Jun 28.

Functionalization of Electron-Rich Secondary Benzyl Alcohols in HFIP: From Thioethers to Trisubstituted Methanes

Martyna Markwitz  1 , Klaudiusz Labrzycki  1 , Kacper Łyczek  1 , Krzysztof Kuciński  1
Affiliations

Functionalization of Electron-Rich Secondary Benzyl Alcohols in HFIP: From Thioethers to Trisubstituted Methanes

Martyna Markwitz et al. J Org Chem. .

Abstract

To date, C-S bond formation via dehydration of electron-rich secondary benzylic alcohols has been limited to catalytic approaches. In this work, we developed an efficient method for synthesizing various thioethers by employing hexafluoroisopropanol (HFIP) as a solvent. This approach also enables the functionalization of secondary benzyl alcohols with other important organic molecules, such as allylsilanes, activated arenes, and indoles, leading to various trisubstituted methanes, including 14 novel products in total.

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Figures

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1. Context of the Investigation
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2. Substrate Scope for Dehydrative Nucleophilic Substitution
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3. Further Investigations
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