Extracurricular laboratory: Discover of C5H4ClN

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A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 626-60-8, Name is 3-Chloropyridine, molecular formula is C5H4ClN. In an article, author is Mannava, Vennela,once mentioned of 626-60-8, Quality Control of 3-Chloropyridine.

Nickel-Mediated Dehydrogenative Aryl-Aryl Homocoupling of a Bulky Phosphino-Pyridine

Aryl-aryl bond formation through dehydrogenative coupling is an attractive transformation due to the atom and step economy of working with unfunctionalized C-H bonds. Pd catalysts are most common for this process, but Ni complexes have also been targeted as less expensive and more abundant alternatives. Here we report the ability of Ni-0 to activate a sterically encumbered phosphino-pyridine ligand with resulting dehydrogenative aryl-aryl homocoupling. The net H-2 equivalent is transferred to the coligand, resulting in hydrogenation of an olefin unit. We have investigated the mechanism of this process by stirring Ni(1,5-COD)(2) (COD = cyclooctadiene) and the PNPh ligand (PNPh = 2-((di-tert-butylphosphino)methyl)-6-phenylpyridine) at mild temperatures to afford a Ni-II complex. Isolation and characterization shows a PNPh ligand coordinated to Ni-II through an activated pyridine carbon and the directing phosphine. The coligand is an activated allylic cyclooctenyl fragment resulting from partial hydrogenation of 1,5-COD. We propose that this intermediate reacts intermolecularly with 1 equiv of itself, enabling the isolation of a bi-PNPh compound (bi-PNPh = 2,2′-bis((di-tert-butylphosphino)methyl)-6,6′-dipheny1-3,3′-bipyridine), coupled through the activated pyridyl position. This dehydrogenative coupling, although stoichiometric, demonstrates the potential of Ni-0-mediated C(sp(2))-H activation and homocoupling for synthetic applications.

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Reference:
Pyridine – Wikipedia,
,Pyridine | C5H5N – PubChem