Synthetic Route of C17H14NP. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: Diphenyl-2-pyridylphosphine, is researched, Molecular C17H14NP, CAS is 37943-90-1, about Non-symmetrical bis-azine biaryls from chloroazines: a strategy using phosphorus ligand-coupling. Author is Boyle, Benjamin T.; Hilton, Michael C.; McNally, Andrew.
Distinct approaches to synthesize bis-azine biaryls are in demand as these compounds have multiple applications in the chem. sciences and are challenging targets for metal-catalyzed cross-coupling reactions. Most approaches focus on developing new reagents as the formal nucleophilic coupling partner that can function in metal-catalyzed processes. We present an alternative approach using pyridine and diazine phosphines as nucleophilic partners and chloroazines where the heterobiaryl bond is formed via a tandem SNAr-phosphorus ligand-coupling sequence. The heteroaryl phosphines are prepared from chloroazines and are bench-stable solids. A range of bis-azine biaryls can be formed from abundant chloroazines using this strategy that would be challenging using traditional approaches. A one-pot cross-electrophile coupling of two chloroazines is feasible, and we also compared the phosphorus-mediated strategy with metal-catalyzed coupling reactions to show advantages and compatibility. Distinct approaches to synthesize bis-azine biaryls are in demand as these compounds have multiple applications in the chem. sciences and are challenging targets for metal-catalyzed cross-coupling reactions. Most approaches focus on developing new reagents as the formal nucleophilic coupling partner that can function in metal-catalyzed processes. We present an alternative approach using pyridine and diazine phosphines as nucleophilic partners and chloroazines where the heterobiaryl bond is formed via a tandem SNAr-phosphorus ligand-coupling sequence. The heteroaryl phosphines are prepared from chloroazines and are bench stable solids. Using this strategy, a range of bis-azine biaryls can be formed from abundant chloroazines that would be challenging using traditional approaches and a one-pot cross-electrophile coupling of two chloroazines is feasible. Thus, e.g., treatment of 2-(diphenylphosphinyl)-6-methylpyridine with 3,4-dichloropyridine, NaOTf, HCl and dioxane followed by HCl in dioxanes, H2O and TFE afforded I (81%).
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Isoquinoline – Wikipedia,
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