Potassium Amide-Catalyzed Benzylic C-H Bond Addition of Alkylpyridines to Styrenes was written by Zhai, Dan-Dan;Zhang, Xiang-Yu;Liu, Yu-Feng;Zheng, Lei;Guan, Bing-Tao. And the article was included in Angewandte Chemie, International Edition in 2018.Formula: C8H11N This article mentions the following:
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 Bronsted 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. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4Formula: C8H11N).
2-Isopropylpyridine (cas: 644-98-4) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Formula: C8H11N