Dehydrative amination of benzhydrols with electron-withdrawing group-substituted 2-aminopyridines utilizing Au(iii)/TPPMS catalyst system in water?
Organic & Biomolecular Chemistry Pub Date: 2022-05-03 DOI: 10.1039/D2OB00673A
Abstract
We report a method for gold(III)/sodium diphenylphosphinobenzene-3-sulfonate (TPPMS)-catalyzed direct amination of benzhydrols using 2-aminopyridines with poor nucleophilic character in water. Various functional groups such as electron-withdrawing nitro, cyano and halogen groups were tolerated well to form the desired N-benzylated 2-aminopyridine compounds. On the basis of mechanistic studies including kinetic profiles, Hammett study and isotope effects, we propose a pathway in which a Lewis acidic gold cation species activates the sp3 C–O bond of the alcohol in the rate-determining step.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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