So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Ma, Xiaoshen; Dang, Hester; Rose, John A.; Rablen, Paul; Herzon, Seth B. researched the compound: 2-Chloropyridine 1-oxide( cas:2402-95-1 ).Safety of 2-Chloropyridine 1-oxide.They published the article 《Hydroheteroarylation of Unactivated Alkenes Using N-Methoxyheteroarenium Salts》 about this compound( cas:2402-95-1 ) in Journal of the American Chemical Society. Keywords: hydroheteroarylation unactivated alkene methoxyheteroarenium salt; alkene addition regioisomer preparation radical mechanism. We’ll tell you more about this compound (cas:2402-95-1).
We report the first reductive coupling of unactivated alkenes with N-methoxy pyridazinium, imidazolium, quinolinium, and isoquinolinium salts under hydrogen atom transfer (HAT) conditions, and an expanded scope for the coupling of alkenes with N-methoxy pyridinium salts. N-Methoxy pyridazinium, imidazolium, quinolinium, and isoquinolinium salts are accessible in 1-2 steps from the com. arenes or arene N-oxides (25-99%). N-Methoxy imidazolium salts are accessible in three steps from com. amines (50-85%). In total 36 discrete methoxyheteroarenium salts bearing electron-donating, electron-withdrawing, alkyl, aryl, halogen, and haloalkyl substituents were prepared (several in multigram quantities) and coupled with 38 different alkenes. The transformations proceed under neutral conditions at ambient temperature, provide monoalkylation products exclusively, and form a single alkene addition regioisomer. Preparatively useful and complementary site selectivities in the addition of secondary and tertiary radicals to pyridinium salts are documented: harder secondary radicals favor C-2 addition (2->10:1), while softer tertiary radicals favor bond formation to C-4 (4.7->29:1). A diene possessing a 1,2-disubstituted and 2,2-disubstituted alkene undergoes hydropyridylation at the latter exclusively (61%) suggesting useful site selectivities can be obtained in polyene substrates. The methoxypyridinium salts can also be employed in dehydrogenative arylation, borono-Minisci, and tandem arylation processes. Mechanistic studies support the involvement of a radical process.
In some applications, this compound(2402-95-1)Safety of 2-Chloropyridine 1-oxide is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.
Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem