While <i>S</i>-aryl thioformates have been utilized as formyl equivalents for palladium-catalyzed Negishi reactions or as mechanistic probes in studying transthioesterification reactions, they remain largely unexplored despite their easy synthesis from thiophenols. We first became interested in the photochemistry of thioformates, including using them as precursors of thiyl radicals to generate sulfoxide products upon addition to alkenes. Additionally, thioformates can be utilized as carbon monoxide surrogates in carbonylation reactions. Fundamental mechanistic investigation has been useful in elucidating these different modes of reactivity to develop synthetically useful transformations. Funding from the American Chemical Society Petroleum Research Fund has been critical in supporting this early-career research in a small liberal arts college setting.

Exploring the chemistry of <i>S</i>-aryl thioformates

ACS Spring 2022

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Exploring the chemistry of S-aryl thioformates