Synthesis of Primary and Secondary Alkylboronates through Site-Selective C(sp3)-H Activation with Silica-Supported Monophosphine-Ir Catalysts was written by Kawamorita, Soichiro;Murakami, Ryo;Iwai, Tomohiro;Sawamura, Masaya. And the article was included in Journal of the American Chemical Society in 2013.Electric Literature of C8H11N This article mentions the following:
The site-selective activation and borylation of unactivated C(sp3)-H bonds in 2-alkylpyridines to form primary and secondary alkylboronates was achieved using silica-supported monophosphine-Ir catalysts. This borylation occurs selectively at C-H bonds located γ to the pyridine nitrogen atom. The site-selectivity of this reaction suggests that the C-H bond cleavage occurs with the assistance of a proximity effect due to N-to-Ir coordination. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4Electric Literature of C8H11N).
2-Isopropylpyridine (cas: 644-98-4) belongs to pyridine derivatives. Pyridine’s the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of pyridine, as it easily supports bond formation via an electrophilic attack. Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C–H in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.Electric Literature of C8H11N