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Potassium Amide‐Catalyzed Benzylic C−H Bond Addition of Alkylpyridines to Styrenes
Author(s) -
Zhai DanDan,
Zhang XiangYu,
Liu YuFeng,
Zheng Lei,
Guan BingTao
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201710128
Subject(s) - chemistry , chemoselectivity , electrophile , trimethylsilyl , amide , catalysis , pyridine , deprotonation , medicinal chemistry , potassium , organic chemistry , yield (engineering) , combinatorial chemistry , ion , materials science , metallurgy
The benzylic functionalization of alkylpyridines is an important pathway for pyridine derivatives synthesis. The reaction partners, however, were mostly limited to highly reactive polar electrophiles. Herein, we report a potassium amide‐catalyzed selective benzylic C−H bond addition of alkylpyridines to styrenes. Potassium bis(trimethylsilyl)amide (KHMDS), a readily available Brønsted base, showed excellent catalytic activity and chemoselectivity. A series of alkylpyridine derivatives, including benzylic quaternary carbon substituted pyridines, were obtained in good to high yield. Preliminary mechanistic studies revealed that the deprotonation equilibrium is probably responsible for the excellent selectivity.