An effective methodology has been developed for the synthesis of enantiopure 2,2′-dialkynylated 1,1′-binaphthalene derivatives. Enantiopure 2,2′-diiodo-1,1′-binaphthalene (10) provided 2,2′-diethynyl-1,1′-binaphthalene (16) in the Negishi alkynylation supported by microwave irradiation in a very good yield with conservation of stereochemical information. The Stephen-Castro alkynylation of 10 afforded products in lower yields; however, in stereoconservative manner as well. Terminal diacetylene 16 served as precursor in the Sonogashira cross-coupling reaction to give new bispyridine derivatives 7-9 as potential ligands in moderate to high yields. Coordination of bispyridines with Zn 2+ and Ag + ions was observed by NMR and CD spectroscopy. The coordination ability of bis(2-pyridylethynyl) derivative 7 to palladium cation was determined by X-ray structure analysis. Keywords: Sonogashira reaction; Alkynylations; Bispyridines; Binaphthalenes; C 2 -Symmetric ligands; Cross-coupling reactions; Palladium; Alkynes; Helicenes; Biaryls.Axial chirality as a unique stereochemical property of axially chiral 1,1′-binaphthalene derivatives substituted at the position 2 and 2′ plays a crucial role in their broad application in stereoselective synthesis 1 , in materials science 2 , in the separation and recognition of chiral compounds 3 . Substitution reactions, in particular cross-coupling reactions, at both positions 2 and 2′ are critical for conservation of stereochemical information in the course of preparation of such derivatives [4][5][6][7] . Specialty of the cross-coupling reactions (or any substitutions) at the positions 2 and 2′ consist in substan-
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