Details

Autor(en) / Beteiligte

• Zhai, Dan‐Dan
• Zhang, Xiang‐Yu
• Liu, Yu‐Feng
• Zheng, Lei
• Guan, Bing‐Tao

Titel

Potassium Amide‐Catalyzed Benzylic C−H Bond Addition of Alkylpyridines to Styrenes

Ist Teil von

• Angewandte Chemie International Edition, 2018-02, Vol.57 (6), p.1650-1653

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2018

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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. The simpler the better: A potassium amide‐catalyzed selective benzylic C−H bond addition of alkylpyridines to styrenes was achieved for the first time. Potassium bis(trimethylsilyl)amide (KHMDS), a simple and readily available Brønsted base catalyst, displayed excellent activity and selectivity for the alkylation of alkylpyridines.