Selective C-C bond formation from rhodium-catalyzed C-H activation reaction of 2-arylpyridines with 3-aryl-2H-azirines was written by Baek, Yonghyeon;Kim, Jinwoo;Hyunseok Kim;Jung, Seung Jin;Ryu, Ho;Kim, Suyeon;Son, Jeong-Yu;Um, Kyusik;Han, Sang Hoon;Seo, Hyung Jin;Heo, Juyoung;Lee, Kooyeon;Baik, Mu-Hyun;Lee, Phil Ho. And the article was included in Chemical Science in 2019.Formula: C12H11N This article mentions the following:
A novel method for the synthesis of acylmethyl-substituted 2-arylpyridine derivatives I [R1 = Ph, 4-MeC6H4, 2-ClC6H4, etc.; R2 = 4-Me, 5-C(O)Me, 5-CF3, etc.; R3 = H, Me, F, C(O)Me, CO2Et] was synthesized via rhodium-catalyzed C-H activation reaction of 3-aryl-2H-azirines with 2-arylpyridines and explored a prototype reaction using DFT-calculations Computational studies quickly revealed and prototype exptl. work confirmed that neither the formation of the expected metal nitrene complexes nor the C-N coupling were viable. Instead, azirine ring-opening followed by C-C coupling was found to be much more favorable to give imines that readily underwent hydrolysis in aqueous conditions to form compounds I. This new method was highly versatile and selective toward a wide range of substrates with high functional group tolerance. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Formula: C12H11N).
2-(m-Tolyl)pyridine (cas: 4373-61-9) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Formula: C12H11N