TY - JOUR
T1 - Pyridine-Boryl Radical-Enabled Reductive Radical Brook Rearrangement
AU - Bai, Wenbo
AU - Luo, Yongwei
AU - Luo, Liuxin
AU - Yuan, Fangxue
AU - Wei, Lanfeng
AU - Li, Pengfei
AU - Xu, Liang
N1 - Publisher Copyright:
© 2026 American Chemical Society
PY - 2026/7/3
Y1 - 2026/7/3
N2 - 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.
AB - 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.
UR - https://www.scopus.com/pages/publications/105043778568
U2 - 10.1021/acs.orglett.6c01570
DO - 10.1021/acs.orglett.6c01570
M3 - 快报
AN - SCOPUS:105043778568
SN - 1523-7060
VL - 28
SP - 8253
EP - 8258
JO - Organic Letters
JF - Organic Letters
IS - 26
ER -