Electric Literature of C24H9F18P. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: Tris(3,5-bis(trifluoromethyl)phenyl)phosphine, is researched, Molecular C24H9F18P, CAS is 175136-62-6, about Palladium-catalysed C-H activation of aliphatic amines to give strained nitrogen heterocycles. Author is McNally, Andrew; Haffemayer, Benjamin; Collins, Beatrice S. L.; Gaunt, Matthew J..
The development of new chem. transformations based on catalytic functionalization of unactivated C-H bonds has the potential to simplify the synthesis of complex mols. dramatically. Transition metal catalysis has emerged as a powerful tool with which to convert these unreactive bonds into carbon-carbon and carbon-heteroatom bonds, but the selective transformation of aliphatic C-H bonds is still a challenge. The most successful approaches involve a ‘directing group’, which positions the metal catalyst near a particular C-H bond, so that the C-H functionalization step occurs via cyclometallation. Most directed aliphatic C-H activation processes proceed through a five-membered-ring cyclometallated intermediate. Considering the number of new reactions that have arisen from such intermediates, it seems likely that identification of distinct cyclometallation pathways would lead to the development of other useful chem. transformations. Here we report a palladium-catalyzed C-H bond activation mode that proceeds through a four-membered-ring cyclopalladation pathway. The chem. described here leads to the selective transformation of a Me group that is adjacent to an unprotected secondary amine into a synthetically versatile nitrogen heterocycle. The scope of this previously unknown bond disconnection is highlighted through the development of C-H amination and carbonylation processes, leading to the synthesis of aziridines and β-lactams (resp.), and is suggestive of a generic C-H functionalization platform that could simplify the synthesis of aliphatic secondary amines, a class of small mols. that are particularly important features of many pharmaceutical agents. E.g., in presence of Pd(OAc)2, PhI(OAc)2, and Ac2O in toluene, aziridination of morpholine derivative (I) gave 74% fused aziridine (II).
This literature about this compound(175136-62-6)Electric Literature of C24H9F18Phas given us a lot of inspiration, and I hope that the research on this compound(Tris(3,5-bis(trifluoromethyl)phenyl)phosphine) can be further advanced. Maybe we can get more compounds in a similar way.
Reference:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem