A Combined IM-MS/DFT Study on [Pd(MPAA)]-Catalyzed Enantioselective C-H Activation: Relay of Chirality through a Rigid Framework was written by Cheng, Gui-Juan;Chen, Ping;Sun, Tian-Yu;Zhang, Xinhao;Yu, Jin-Quan;Wu, Yun-Dong. And the article was included in Chemistry – A European Journal in 2015.Application In Synthesis of 2-Isopropylpyridine This article mentions the following:
A combined ion-mobility mass spectrometry (IM-MS) and DFT study has been employed to investigate the mechanism and the origin of selectivity of palladium/mono-N-protected amino acid (MPAA)-catalyzed enantioselective C-H activation reactions of several prochiral substrates. We captured the [Pd(MPAA)(substrate)] complex at different stages, and demonstrated that the C-H bond can be activated in the absence of an external base. DFT studies lead to the establishment of a significantly modified relay mechanism invoking a key conformational effect to account for the origin of enantioselectivity. This relay mechanism successfully accounts for the enantioselectivity for all the relevant reactions reported. The enantioselectivity originates from the rigid square-planar Pd coordination in the C-H activation transition state: Bidentate MPAA and substrate coordination. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4Application In Synthesis of 2-Isopropylpyridine).
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. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Application In Synthesis of 2-Isopropylpyridine