An efficient transition-metal-free route to oligo-?-pyridylamines via fluoroarenes
COMPTES RENDUS CHIMIE(2023)
摘要
The new polynucleating tripodal proligand H6tren(dpa)3, containing thirteen nitrogen donors of four different types, was designed, synthesized, and isolated in good yield (similar to 60%) via a transition-metal-free triple N-arylation of H6tren with HXdpa (X = Br or F), using K2CO3 or Cs2CO3 as a base (H6tren = tris(2-aminoethyl)amine, HXdpa = 6-halogeno-N-(pyridin-2-yl)pyridin-2-amine). HFdpa was prepared with excellent yield (90-92%) by reaction of 2,6-difluoropyridine with 2-aminopyridine in LiH/toluene/pyridine and was found more reactive than HBrdpa, affording higher conversion and higher yield. Use of Cs2CO3 turned out to be essential for achieving high regioselec-tivity and eliminating overarylation almost completely.
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关键词
Oligo-?-pyridylamides,Tripodal ligands,Halopyridines,Metal-free,Buchwald-Hartwig,EMACs
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