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Experimental study demonstrates efficient dehydroxylative cross-coupling of 4-hydroxypyridines with disulfides, suggesting a scalable route to diverse pyridyl thioethers.
An efficient dehydroxylative cross-electrophile coupling of 4-hydroxypyridines with disulfides by employing diphenylphosphine oxide as an activator was developed. The thiolative protocol proceeded effectively via the cleavage of a relatively inert C–OH bond to produce a wide plethora of pyridyl thioethers in moderate to excellent yields. The coupling protocol could also be scaled up with ease and successfully applied to the utilization of diselenide as a substrate. Mechanistic exploration disclosed that in situ-generated S-aryl diphenylphosphinothioate from the reaction of diaryl disulfide with diphenylphosphine oxide presumably functions as the pivotal intermediate of the thioetherification.
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Tang et al. (2026) studied this question.
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