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Decoupling Deprotonation from Metalation: Thia-Fries Rearrangement


  • We thank AstraZeneca and the MEC (Spain) for generous funding.


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Label-enabled: Studies with 2H-, 18O-, and 34S-labeled aryl triflates show that lithium diisopropylamide-mediated thia-Fries rearrangement proceeds through an irreversible ortho deprotonation (see scheme; DIPA=diisopropylamine, LDA=lithium diisopropylamide). In contrast, ortho metalation results exclusively in the generation of a benzyne.

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