Pd(0)-catalyzed amination in the synthesis of chiral derivatives of BINAM and their evaluation as fluorescent enantioselective detectors

Abstract

A mini-review covers recent successes in the synthesis of (S)-1,1′-binaphthyl-2,2′-diamine (BINAM) using Pd(0)-catalyzed amination reactions. As a result, versatile compounds with C2-chiral backbone were synthesized, among them are derivatives bearing additional chiral amino and fluorophore groups like dansyl amide, 7-methoxycoumarin, 6-aminoquinoline, different macrocyclic compounds with oxadiamine and polyamine linkers were obtained as well. BINAM derivatives of various structures were evaluated as fluorescent enantioselective detectors for a series of model amino alcohols. Many of them were shown to be efficient in sensing certain enantiomers of the amino alcohols by selective changes in the emission in the presence of these analytes. Small changes in the structure of the BINAM derivatives lead to serious difference in the recognition ability of the compounds under investigation.

Spectroscopic Study of a Novel Binaphthyl Amine Fluorescent Probe for Chiral Recognition of DL-Lysine

“…BINAM has long been considered by researchers as a potential fluorescent detector for the efficient chiral recognition of αphenylethylamine and tryptophan enantiomers. [28] Previous studies have shown that probes based on BINAM can highly selectively recognize lysine in aqueous solutions, but the results indicated a significant fluorescent response for both configurations, thus unable to distinguish the configuration of lysine. [29] This article reports the discovery and synthesis of an innovative fluorescent probe, which demonstrates exceptional selectivity for L-lysine under physiological conditions.…”

Spectroscopic Study of a Novel Binaphthyl Amine Fluorescent Probe for Chiral Recognition of DL-Lysine

“…BINAM has long been considered by researchers as a potential fluorescent detector for the efficient chiral recognition of α-phenylethylamine and tryptophan enantiomers. [25] Previous studies have shown that probes based on BINAM can highly selectively recognize lysine in aqueous solutions, but the results indicated a significant fluorescent response for both configurations, thus unable to distinguish the configuration of lysine. [26] This article has discovered and synthesized a fluorescent probe that can selectively recognize L-lysine with high selectivity in physiological conditions.…”

Electrochemical Synthesis of 1,1′-Binaphthalene-2,2′-Diamines via Transition-Metal-Free Oxidative Homocoupling

“…In contrast, the carbon-platinum [32] and fluorine-doped tin oxide(FTO) [33] electrodes gave 2a in 43% and 29% yields, respectively, with low current efficiencies (entries 2 and 3). Other alcoholic reaction solvents, such as methanol, ethanol, and trifluoroethanol, reduced the yield of 2a to 6-12% with current efficiencies of 4-8% (entries 4-6), along with a 5% yield of aza [5] helicene. HFIP, an appropriate solvent for the reaction, serves as an excellent hydrogen bond donor and provides highly persistent radical cations [34,35].…”

“…1,1 -Bi-2-naphthylamine (BINAM) and its derivatives are widely used as building blocks for transition-metal ligands and organocatalysts [1][2][3][4], as well as chiroptical materials for fluorescence sensing [5][6][7]. Among their syntheses, transition-metal mediated coupling of 2-naphthylamine derivatives has been well established [8][9][10][11][12].…”