Reductive radical rearrangement produces functionalized silyl ethers from N-alkoxyphthalimides, suggesting a simple synthetic route.
Herein, we report a reductive radical Brook rearrangement enabled by a pyridine-boryl radical system, utilizing readily available N -alkoxyphthalimides as precursors. This protocol proceeds via a radical cascade of formal single-electron reduction, N–O bond fragmentation, and 1,2-silyl migration. This cascade affords nucleophilic α-silyloxy carbon radicals, which are efficiently intercepted by electron-deficient alkenes to deliver functionalized silyl ethers. The method features stable precursors, operational simplicity, and mild, thermal, metal-free, and oxidant-free conditions.
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Bai et al. (2026) studied this question.
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