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![[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Pyridine-Boryl Radical-Enabled Reductive Radical Brook Rearrangement
Wenbo Bai1, Yongwei Luo1, Liuxin Luo1
1Key Laboratory of Silicon Chemical New Materials, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi 832003, China.
Abstract:
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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