Synthesis of Phenanthridines via a Rhodium-Catalyzed C-C Bond Cleavage Reaction of Biphenylene with Nitriles was written by Korotvicka, Ales;Frejka, David;Hampejsova, Zuzana;Cisarova, Ivana;Kotora, Martin. And the article was included in Synthesis in 2016.Recommanded Product: 6-Fluoropicolinonitrile This article mentions the following:
The reaction of biphenylene with various nitriles in the presence of catalytic amount of bis[(1,2,5,6-η)-1,5-cyclooctadiene]rhodium(1+) tetrafluoroborate(1-) [i.e., [Rh(cod)2BF4]] and dppe under microwave irradiation afforded 9-substituted phenanthridines. The reaction with alkyl and aromatic nitriles provided the corresponding 9-substituted phenanthridines in 26-79% isolated yields. The reaction was also carried out with cyanopyridines and it provided heterocyclic compounds with the bipyridine and terpyridine scaffold. The synthesized bipyridine and terpyridine were complexed with [Rh(cod)Cl]2. The former provided a Rh(III) complex in which the cyclooctadiene moiety was oxidized to the THF ring, whereas the latter gave a structurally fluxional complex (in solution) with only one pyridine ring coordinated to the rhodium atom. The title compounds thus formed included 6-(3-chlorophenyl)phenanthridine, 3-(6-phenanthridinyl)benzonitrile, 6-(2-thienyl)phenanthridine (thiophene), 6-(2-furanyl)phenanthridine (furan), 6-(2-pyridinyl)phenanthridine. The synthesis of the target compound was achieved by a reaction of 6-(2-pyridinyl)phenanthridine (i.e., a bipyridine analog) with di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]dirhodium [i.e., [Rh(COD)Cl]2 cyclooctadiene-group oxidation]. The title compound thus formed was a 9-Oxabicyclo[4.2.1]nonane-(pyridinyl)phenanthridine-rhodium complex. In the experiment, the researchers used many compounds, for example, 6-Fluoropicolinonitrile (cas: 3939-15-9Recommanded Product: 6-Fluoropicolinonitrile).
6-Fluoropicolinonitrile (cas: 3939-15-9) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Recommanded Product: 6-Fluoropicolinonitrile