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Sodium template synthesis of a 54-membered bis(pyridine) macrocycle

Abstract : An operationally simple and high yielding sodium-template-based synthesis of a large bis(pyridine)-based macrocycle is described. Complexation of two equivalents of 2,6-bis(10-undecen-1-oxymethyl)-pyridine with Na[BAr F 4 ] (Ar F = 3,5-C 6 H 3 (CF 3) 2) enabled the selective cross-metathesis of the terminal alkene substituents and formation of the corresponding bis(pyridine) macrocycle in 51% isolated yield. The new 54-membered macrocycle was characterized in the solid-state by X-ray diffraction in addition to verification of the structure in solution by NMR spectroscopy and ESI-MS.
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Thibault Troadec, Amber Thompson, Adrian Chaplin. Sodium template synthesis of a 54-membered bis(pyridine) macrocycle. Tetrahedron Letters, Elsevier, 2015, 56 (31), pp.4613-4615. ⟨10.1016/j.tetlet.2015.05.110⟩. ⟨hal-01646159⟩



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