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Syntheses are reported for tripyridine macrocycles 2 and 3 and some of their alkyl derivatives. The macrocycles are designed to stabilize to various extents coordinated d8 metal precursors and d6 alkane oxidative addition products (ptIV), therefore allowing favorable kinetics and thermodynamics of (e.g., PtII) the cleavage of substrate H-C(sp3) bonds. Both the Chichibabin protocol and oxidative coupling of carbanions by copper(I) iodide were used for the macrocyclization step. Crystal structures of singly and doubly protonated 2 establish atom connectivity in the macrocycle, and reveal structural features which are obscured in solution NMR by rapid proton migration.
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Reference：
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis