16303-15-4

Upstream product

• 1532-72-5 isoquinoline N-oxide 
• 981-18-0 triphenyl(phenylazo)methane 
• 71-43-2 benzene 
• 3297-72-1 1-phenylisoquinoline 
• 100-63-0 phenylhydrazine 
• 591-50-4 iodobenzene 
• 22960-55-0 isoquinoline 1-carboxylic acid N-oxide 
• 486-73-7 1-isoquinolinecarboxylic acid 

Downstream Products

• 16303-14-3 2-phenyl-benzo[f][1,3]oxazepine 
• 3297-72-1 1-phenylisoquinoline 

Relevant academic research and scientific papers

Visible-light-promoted c2 selective arylation of quinoline and pyridine n-oxides with diaryliodonium tetrafluoroborate

A protocol of visible-light-promoted C2 selective arylation of quinoline and pyridine N-oxides, with diaryliodonium tetrafluoroborate as an arylation reagent, using eosin Y as a photocatalyst for the construction of N-heterobiaryls was presented. This met

KMnO4-mediated direct C2-selective C?H arylation of quinoline N-oxides with aromatic hydrazines

An efficient protocol for the synthesis of 2-arylquinoline N-oxides has been developed via KMnO4-mediated cross-coupling reaction of quinoline N-oxides with aromatic hydrazines in moderated to good yields. The reactions proceeded efficiently over a broad range of substrates with excellent regioselectivity and functional group tolerance.

Hydroheteroarylation of Unactivated Alkenes Using N-Methoxyheteroarenium Salts

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 commercial arenes or arene N-oxides (25-99%). N-Methoxy imidazolium salts are accessible in three steps from commercial 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 pyidinium 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.

Regioselective decarboxylative cross-coupling of carboxy isoquinoline N -oxides

A straightforward method for direct decarboxylative arylation of 1- and 3-carboxy isoquinaldic acid N-oxides with aryl iodides is reported. The reaction proceeded selectively at the carboxy function site to exclusively give the corresponding C-1/sub

Palladium-catalyzed C-H functionalization of pyridine N-oxides: Highly selective alkenylation and direct arylation with unactivated arenes

Two catalytic protocols of the oxidative C-C bond formation have been developed on the basis of the C-H bond activation of pyridine N-oxides. Pd-catalyzed alkenylation of the N-oxides proceeds with excellent regio-, stereo-, and chemoselectivity, and the